JPH04154707A - Complex antimicrobial insecticide - Google Patents
Complex antimicrobial insecticideInfo
- Publication number
- JPH04154707A JPH04154707A JP2276557A JP27655790A JPH04154707A JP H04154707 A JPH04154707 A JP H04154707A JP 2276557 A JP2276557 A JP 2276557A JP 27655790 A JP27655790 A JP 27655790A JP H04154707 A JPH04154707 A JP H04154707A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- dimethyl
- dichloro
- chlorophenyl
- fungicidal
- 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 23
- 230000000845 anti-microbial effect Effects 0.000 title 1
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 29
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002131 composite material Substances 0.000 claims description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 claims description 4
- YTYCXVWQVDXSKV-UHFFFAOYSA-N 2,2-dichloro-n-[1-(4-chlorophenyl)ethyl]-1-propan-2-ylcyclopropane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(C(C)C)CC1(Cl)Cl YTYCXVWQVDXSKV-UHFFFAOYSA-N 0.000 claims description 2
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- RXDMAYSSBPYBFW-UHFFFAOYSA-N carpropamid Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(CC)C(C)C1(Cl)Cl RXDMAYSSBPYBFW-UHFFFAOYSA-N 0.000 claims description 2
- HRBKVYFZANMGRE-UHFFFAOYSA-N chlorpyrifos-methyl Chemical compound COP(=S)(OC)OC1=NC(Cl)=C(Cl)C=C1Cl HRBKVYFZANMGRE-UHFFFAOYSA-N 0.000 claims description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims description 2
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 claims description 2
- YLQFONACDCMTAX-UHFFFAOYSA-N 2,2-dichloro-n-[1-(4-chlorophenyl)ethyl]-1,3,3-trimethylcyclopropane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(C)C(C)(C)C1(Cl)Cl YLQFONACDCMTAX-UHFFFAOYSA-N 0.000 claims 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 claims 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
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- WSORODGWGUUOBO-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphoryl)thio]succinate Chemical compound CCOC(=O)CC(SP(=O)(OC)OC)C(=O)OCC WSORODGWGUUOBO-UHFFFAOYSA-N 0.000 claims 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 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
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 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
- 150000003839 salts Chemical class 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
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 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
- 238000002054 transplantation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は公知の殺菌性カルボキサミド類又はその光学異
性体と、公知の殺虫性有機リン酸エステル類とから成る
殺菌殺虫活性を有する新規複合殺菌殺虫剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel composite fungicidal and insecticide having fungicidal and insecticidal activity, which is composed of known fungicidal carboxamides or optical isomers thereof and known insecticidal organophosphate esters.
本願出願日前公知の特開昭61−15867号、同62
−201855号及び特開平2−11550号には、本
発明に係わるところの殺菌性カルボキサミド類及びその
光学異性体が記載されている。JP-A-61-15867 and JP-A-62, which were known before the filing date of the present application.
-201855 and JP-A-2-11550 describe fungicidal carboxamides and optical isomers thereof, which are related to the present invention.
水稲栽培は近年、稚苗移植機による機械移植が広く行な
われており、水稲本田に於ける害虫並びに作物病の同時
防除と共に、薬剤の育苗箱施用による害虫及び作物病の
同時防除並びに省力化が望まれている。In recent years, mechanical transplantation using seedling transplanters has been widely used for paddy rice cultivation, and it is possible to simultaneously control pests and crop diseases in paddy rice plants, and to simultaneously control pests and crop diseases by applying chemicals to seedling boxes, as well as to save labor. desired.
また、農薬使用量及び使用回数の低減が、安全性並びに
環境保全の面から、強く望まれており、より一層の低薬
量での使用が検討されている。In addition, there is a strong desire to reduce the amount and frequency of use of pesticides from the standpoint of safety and environmental conservation, and the use of even lower doses of pesticides is being considered.
特に稲栽培に於いて、重要な防除対象害虫である例えば
、鞘翅目害虫(イネミズゾウムシ等)、半翅目害虫(ウ
ンカ、ヨコバイ類)、並びに重要な防除対象病害である
イモチ病の同時防除、省力化及びより一層の安全面での
改善が期待されている。Particularly in rice cultivation, simultaneous control of important pests to be controlled, such as Coleoptera pests (rice weevils, etc.), Hemiptera pests (planthoppers, leafhoppers), as well as rice blast disease, which is an important pest to be controlled, and labor saving. It is expected that this will lead to improved safety and further improvements in safety.
この度、本発明者等は、
式:
式中、Zはハロゲン原子を示し、
R1は炭素数1〜4のアルキル基を示し、Rzは水素原
子、メチル基又はエチル基を示し、
そして
R3は水素原子又はメチル基を示す、
で表わされる殺菌性カルボキサミド類又はその光学異性
体と、
0.0−ジメチル 0−4−メチルチオ−m−トリルホ
スホロチオエート、
0.0−ジメチル 0−4−ニトロ−m−トリルホスホ
ロチオエート、
4−(メチルチオ)フェニル ジプロピルホスフェート
、
〇−エチル 0−4−ニトロフェニル フェニルホスホ
ノチオエート、
02o−ジメチル S、2−エチルチオエチルホスホロ
ジチオエート、
S−α−エトキシカルボニルベンジル 0.0−ジメチ
ルホスホロジチオエート、
S−1,2−ビス(エトキシカルボニル)エチル0.0
−ジメチルホスホロチオエート、0.0−ジメチル S
−メチルカルバモイルメチルホスホロジチオエート、
0、O−ジメチル 5−2− (1−メチルカルバモイ
ルエチルチオ)エチルホスホロチオエート、ジメチル
2,2.2− )ジクロロ−1−ヒドロキシエチルホス
ホネート、
1.2−ジブロモ−2,2−ジクロロエチル ジメチル
ホスフェート、
2.2−ジクロロビニルジメチルホスフェート、2−ク
ロロ−1−(2,4−ジクロロフェニル)ビニルジエチ
ルホスフェート、
(Z)−2−クロロ−1−(2,4,5−トリクロロフ
ェニル)ビニル ジメチルホスフェート、ジメチル (
E)−1−メチル−2−(メチルカルバモイル)ビニル
ホスフェート、
0.0−ジメチル O−3,5,6−)ジクロロ−2−
ピリジルホスホロチオエート、
0−2−ジエチルアミノ−6−メチルピリミジン−4−
イル 0.o−ジメチルホスホロチオエート、
0.0−ジエチル 0 2−iso−プロピル−6−メ
チルピリミジン−4−イルホスホロチオエート、
0.0−ジエチル O−2,3−ジヒドロ−3−オキソ
−2−フェニル−6−ピリダジニルホスホロチオエート
、
0.0−ジエチル 0−5−フェニルイソキサゾール−
3−イルホスホロチオエート、S−2,3−ジヒドロ−
5−メトキシ−2−オキソ−1,3,4−チアジアゾー
ル−3−イルメチル0.0−ジメチルホスホロジチオエ
ート、2−メトキシ−4H−1,3,2λ5−ベンゾジ
オキサホスホリン−2−サルファイド、
及びO−(1−(4−クロロフェニル)−LH−ピラゾ
ール−4−イル〕0−エチル S−プロピルホスホロチ
オエート
より成る公知殺虫性化合物群から選ばれる一種とを有効
成分として含有することから成る新規複合殺菌殺虫剤が
、優れた殺菌殺虫作用を示すことを見い出した。This time, the present inventors have developed the following formula: In the formula, Z represents a halogen atom, R1 represents an alkyl group having 1 to 4 carbon atoms, Rz represents a hydrogen atom, a methyl group, or an ethyl group, and R3 represents hydrogen. A fungicidal carboxamide or an optical isomer thereof, which represents an atom or a methyl group, and 0.0-dimethyl 0-4-methylthio-m-tolyl phosphorothioate, 0.0-dimethyl 0-4-nitro-m- Tolyl phosphorothioate, 4-(methylthio)phenyl dipropyl phosphate, 〇-ethyl 0-4-nitrophenyl phenylphosphonothioate, 02o-dimethyl S, 2-ethylthioethyl phosphorodithioate, S-α-ethoxycarbonylbenzyl 0 .0-dimethylphosphorodithioate, S-1,2-bis(ethoxycarbonyl)ethyl 0.0
-dimethyl phosphorothioate, 0.0-dimethyl S
-Methylcarbamoylmethylphosphorodithioate, 0,O-dimethyl 5-2- (1-methylcarbamoylethylthio)ethylphosphorothioate, dimethyl
2,2.2-) dichloro-1-hydroxyethyl phosphonate, 1.2-dibromo-2,2-dichloroethyl dimethyl phosphate, 2.2-dichlorovinyl dimethyl phosphate, 2-chloro-1-(2,4- dichlorophenyl) vinyl diethyl phosphate, (Z)-2-chloro-1-(2,4,5-trichlorophenyl) vinyl dimethyl phosphate, dimethyl (
E) -1-Methyl-2-(methylcarbamoyl)vinyl phosphate, 0.0-dimethyl O-3,5,6-)dichloro-2-
Pyridyl phosphorothioate, 0-2-diethylamino-6-methylpyrimidine-4-
Il 0. o-dimethyl phosphorothioate, 0.0-diethyl 0 2-iso-propyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0-diethyl O-2,3-dihydro-3-oxo-2-phenyl-6- Pyridazinyl phosphorothioate, 0.0-diethyl 0-5-phenylisoxazole-
3-yl phosphorothioate, S-2,3-dihydro-
5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl 0.0-dimethylphosphorodithioate, 2-methoxy-4H-1,3,2λ5-benzodioxaphosphorine-2-sulfide , and one selected from the group of known insecticidal compounds consisting of O-(1-(4-chlorophenyl)-LH-pyrazol-4-yl]0-ethyl S-propylphosphorothioate as an active ingredient. It has been found that a composite fungicidal and insecticidal agent exhibits excellent bactericidal and insecticidal effects.
本発明によれば、本発明の複合殺菌殺虫側は意外にも、
驚くべきことには、前記式(I)の殺菌性カルボキサミ
ド類又はその光学異性体、及び前記公知殺虫性化合物を
夫々、単独で使用した場合に比較し、害虫並びに作物病
の同時防除を可能にすることはもちろん、単独の使用に
よる作用効果からは側底予想し得ない、混合による協力
及び相乗効果を現わし、それによって、より低薬量で格
別顕著な殺菌殺虫効果を現わすことができる。そして本
発明の複合殺菌殺虫剤は、特には、稲の主要害虫であっ
て、また既存薬剤(有機リン系並びにカーバメート系殺
虫剤)に抵抗性を獲得した半翅目害虫のウンカ・ヨコバ
イ類、鞘翅目害虫のイネミズゾウムシ等、鱗翅目害虫の
コブノメイガ等並びに稲に対する最大の病害であるいも
ち病に対し、同時且つ的確に、卓越した作用効果を現わ
す。According to the present invention, the composite bactericidal and insecticidal side of the present invention surprisingly has the following properties:
Surprisingly, the fungicidal carboxamides of formula (I) or their optical isomers and the known insecticidal compounds can simultaneously control pests and crop diseases compared to when used alone. Of course, they also exhibit cooperative and synergistic effects when mixed, which cannot be expected from the effects of using them alone, and as a result, it is possible to exhibit exceptional bactericidal and insecticidal effects at lower doses. . The composite fungicidal insecticide of the present invention is particularly suitable for planthoppers and leafhoppers, which are major pests of rice and have acquired resistance to existing pesticides (organophosphorus and carbamate pesticides). Simultaneously and precisely, it exhibits outstanding effects against the Coleoptera pests such as the rice weevil, the Lepidoptera pests such as the corn borer moth, and blast disease, the biggest disease of rice.
本発明の複合殺菌殺虫剤に於ける殺菌活性成分の式(I
)に於いて、好ましくは、
Zはクロルを示し、
R1はメチル、エチル、n−プロピル又はイソプロピル
を示し、
R2は水素原子又はメチルを示し、そしてR3は水素原
子又はメチルを示す。The formula (I
), preferably Z represents chloro, R1 represents methyl, ethyl, n-propyl or isopropyl, R2 represents a hydrogen atom or methyl, and R3 represents a hydrogen atom or methyl.
式(n)の化合物の具体例としては、例えばN−Cl−
C4−ブロモフェニル)−エチル]−2,2−ジクロロ
−1,3,3−トリメチルシクロプロパンカルボキサミ
ド、
N−(1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1,3,3−トリメチルシクロプロパンカ
ルボキサミド、
N−C1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1−エチル−3−メチルシクロプロパンカ
ルボキサミド、
N−(1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1−イソプロピルシクロプロパンカルボキ
サミド、
N−(R)−(1−(4−クロロフェニル)−エチル)
−2,2−ジクロロ−1−エチル−3t−メチル−1
r−シクロプロパンカルボキサミドのジアステレオマー
類の混合物、
N−(R)−(1−(4−クロロフェニル)−エチル)
−2,2−ジクロロ−1−イソプロピルシクロプロパン
カルボキサミドのジアステレオマー類の混合物、
N−(R)−(1−(4〜クロロフエニル)−エチル)
−(I 5)−2,2−ジクロロ−1−エチル−3t
−メチル−1r−シクロプロパンカルボキサミド、及び
N−(R)−(1−(4−クロロフェニル)−エチル)
−(Is)−2,2−ジクロロ−1−イソプロピルシク
ロプロパンカルボキサミド
を例示でき、これらの化合物は前掲の特開昭61−15
867号、同62−201855号及び特開平2−11
550号記載の公知化合物である。Specific examples of the compound of formula (n) include, for example, N-Cl-
C4-bromophenyl)-ethyl]-2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N-(1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N-C1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1-ethyl-3-methylcyclopropanecarboxamide, N-(1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1-isopropylcyclopropanecarboxamide, N-(R)-(1-(4-chlorophenyl)-ethyl)
-2,2-dichloro-1-ethyl-3t-methyl-1
Mixture of diastereomers of r-cyclopropanecarboxamide, N-(R)-(1-(4-chlorophenyl)-ethyl)
-Mixture of diastereomers of 2,2-dichloro-1-isopropylcyclopropanecarboxamide, N-(R)-(1-(4-chlorophenyl)-ethyl)
-(I5)-2,2-dichloro-1-ethyl-3t
-methyl-1r-cyclopropanecarboxamide, and N-(R)-(1-(4-chlorophenyl)-ethyl)
-(Is)-2,2-dichloro-1-isopropylcyclopropane carboxamide is an example, and these compounds are disclosed in the above-mentioned JP-A-61-15.
No. 867, No. 62-201855 and JP-A-2-11
It is a known compound described in No. 550.
本発明の複合殺菌殺虫剤に於ける、前記公知殺虫性有機
リン酸エステル類は、例えば、ベスティサイドマニュア
ル第8版1987年(The Br1tishCrop
Protection Counci1発行)、農薬
要覧(1988年)に記載されるものである。The known insecticidal organophosphate esters in the composite fungicidal and insecticide of the present invention are described, for example, in the Besticide Manual, 8th edition, 1987 (The Br1tish Crop
Protection Council 1), Pesticide Directory (1988).
本発明に於いて、複合殺菌殺虫剤に於ける殺菌性化合物
群と殺虫性化合物群との重量比は比較的に広い範囲内で
変えることができる。In the present invention, the weight ratio of the fungicidal compounds to the insecticidal compounds in the composite fungicidal and insecticide can be varied within a relatively wide range.
概して、活性化合物式(1)の殺菌性カルボキサミド類
又はその光学異性体1重量部当り、公知殺虫性化合物0
.5〜10重量部、好ましくは1〜8重量部が使用され
る。In general, 0 parts by weight of the active compound of the fungicidal carboxamides of formula (1) or of their optical isomers of known insecticidal compounds.
.. 5 to 10 parts by weight are used, preferably 1 to 8 parts by weight.
然し、ここに挙げられた重量比は、害虫並びに病害の発
生の程度により、必要に応じて、変えることが可能であ
る。However, the weight ratios listed here can be changed as necessary depending on the degree of occurrence of pests and diseases.
本発明による複合殺菌殺虫剤は、優れた殺菌及び殺虫活
性作用を示し、殺菌殺虫剤として例えば茎葉散布、水中
又は水面施用、土壌施用、土壌混和処理、育苗箱施用等
により使用することができる。The composite fungicidal insecticide according to the present invention exhibits excellent bactericidal and insecticidal activity, and can be used as a bactericidal insecticide by, for example, spraying on foliage, applying in water or on the surface of water, applying to soil, mixing with soil, applying in seedling boxes, etc.
本発明による複合殺菌殺虫剤は、強力な殺菌殺虫作用を
現わす、従って、殺菌殺虫剤として使用することができ
る。そして、本発明による活性化合物は栽培植物に対し
て薬害がなく、かつ温血動物に対する毒性も低く、農業
、特には稲の保護に於ける病害虫、とくに害虫類及び病
害類を的確に防除するために使用できる。それらは、通
常、感受性及び抵抗性の種、そして全ての又はある成長
段階に対して活性である。The composite fungicidal and insecticide according to the present invention exhibits a strong bactericidal and insecticidal action, and therefore can be used as a fungicidal and insecticide. Moreover, the active compound according to the present invention has no phytotoxicity to cultivated plants and has low toxicity to warm-blooded animals, and can be used to accurately control pests and diseases in agriculture, particularly in the protection of rice. Can be used for They are usually active against sensitive and resistant species and against all or some growth stages.
上記した病害虫類(病害及び害虫)として、例えば次の
ものが包含される。そのような病害虫の例としては以下
の如き病害虫類を例示することができる。The above-mentioned pests (diseases and pests) include, for example, the following: Examples of such pests include the following.
病害類としては、PIasa+odiophoromy
cetes (ネコブカビ類) 、Oomycete
s (印画[) 、Chytridio−mycete
s (ツボカビ類) 、Zygomycetes
(接合菌類) 、Ascomycetes (子嚢菌
類) 、Basidiomyce−tes (担子菌類
) 、Deuteromycetes (不完全菌類)
を挙げることができる。特に不完全菌類に属するイネい
もち病菌(Pyricularia oryzae)を
本発明の複合殺菌殺虫剤の殺菌スペクトルとして、挙げ
ることができる。As a disease, PIasa + odiophoromy
cetes, Oomycete
s (Print [), Chytridio-mycete
s (chytrid fungi), Zygomycetes
(Zygomycetes), Ascomycetes (Ascomycetes), Basidiomyce-tes (Basidiomycetes), Deuteromycetes (Deuteromycetes)
can be mentioned. In particular, rice blast fungus (Pyricularia oryzae) belonging to Deuteromycetes can be mentioned as part of the fungicidal spectrum of the composite fungicidal and insecticide of the present invention.
昆虫類として、鞘翅目害虫、例えば
イネミズゾウムシ(Lissorhoptrus or
yzophilus)、イネゾウムシ(Echinoc
inewus squameus) 、イネドロオイム
シ(Oulema oryzae) ;鱗翅目出、例え
ば
ニカメイチュウ(Chilo 5uppressali
s) 、:]プノメイガ(Cnaphalocroci
s +*edinalis) 、、フタオビコガヤ(N
aranga aenescens)、イチモンジセセ
リ(Parnara guttata) ;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 lugens) 、ヒメトビウンカ(Laode
lphax 5triatellus) 、セジロウン
カ(Sogatella furcifera)、アオ
ヵメムシ(Nezara spp、) ; ’
直翅目虫、例えば
ケラ(Gryl−1otalpa africana)
、バッタ(Locus tamigratoria
+sigratoriodes)’ ;等を挙げるこ
とができる。Insects include Coleoptera pests, such as the rice weevil (Lissorhoptrus or
yzophilus), rice weevil (Echinoc)
inewus squameus), Oulema oryzae; Lepidoptera, such as Chilo 5uppressali
s) , :] Cnaphalocroci
s + *edinalis),, Futaobikogaya (N
aranga aenescens), Parnara guttata; Hemiptera,
For example, the black leafhopper (Nephotettix cinc)
ticeps), brown planthopper (Nilaparva)
ta lugens), Laodea planthopper (Laode
lphax 5triatellus), brown planthopper (Sogatella furcifera), green stink bug (Nezara spp,)
, Locus tamigratoria
+sigratoriodes)';
本発明の複合殺菌殺虫剤は、式(I)の活性化合物と公
知殺虫性化合物との混合物の形で、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
ルシヨン、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(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(Mar
mmoist))を挙げることができる。The complex fungicidal insecticides of the invention can be put into customary formulations in the form of mixtures of the active compounds of formula (I) and known insecticidal compounds. Such forms include solutions, emulsions, suspensions, powders, wettable powders, foams, pastes,
Granules, aerosols, active compound infiltration - natural and synthetic,
Microcapsules, seed coatings, preparations with combustion devices, such as combustion devices (fumigation and fume cartridges, cans and coils), and ULV (cold mist, warm mist)
mmoist)).
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、拡展剤、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/又は分散側
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。拡展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 method comprises, for example, combining the active compound with a spreading agent, 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 dispersing agent and/or a carrier. Alternatively, it can be carried out by mixing using a foam forming agent. When using water as extender, for example, organic solvents can also be used as co-solvents.
液体希釈剤又は担体としては、例えば、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 include, for example, aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (
For example, 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, esters, etc.) ), 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素類のようなエアゾ
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, and include, for example, 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、チョーク、石英、アクパルガイド、
モンモリロナイト、又は珪藻土等)、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, chalk, quartz, acpal guide,
montmorillonite, diatomaceous earth, 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粉、そして有機物質細粒体
(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 powders of inorganic and organic powders, and fine granules of organic substances (e.g. , sawdust, coconut shells, corncobs and tobacco stalks).
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
類、ポリオキシエチレン脂肪酸アルコールエーテル類(
例えば、アルキルアリールポリグリコールエーテル類、
アルキルスルホン酸塩類、アルキル硫酸塩類、アリール
スルホン酸塩類等)〕、アルブミン加水分解生成物を挙
げることができる。Examples of emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (
For example, alkylaryl polyglycol ethers,
(alkyl sulfonates, alkyl sulfates, aryl sulfonates, 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。Fixing agents can also be used in the formulations (powders, granules, emulsions), such fixing agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. I can do it.
着色剤を使用することもでき、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、ポロン、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。Coloring agents may also be used, including 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 Mention may be made of such trace elements as their salts of , manganese, poron, 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.
本発明の複合殺菌殺虫剤は、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、殺菌剤、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、カーポキシレート系薬剤、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。−
更に、本発明の複合殺菌殺虫剤は、協力剤との混合剤と
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できる。該協力剤
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。The complex fungicidal insecticides of the present invention are commercially useful formulations thereof and the use forms prepared by these formulations.
Other active compounds, such as insecticides, fungicides, fungicides,
It can also be present as a mixture with growth regulators or herbicides. Here, examples of the insecticide include organic phosphorus agents, carbamate agents, carpoxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced from microorganisms. - Furthermore, the composite fungicidal and insecticide of the present invention can also be present as a mixture with a synergist, and such formulations and usage forms can 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.
本発明の複合殺菌殺虫剤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 in the commercially useful use forms of the complex fungicidal and pesticides of the invention can vary within wide limits.
本発明の複合殺菌殺虫剤の使用上の濃度は、例えば0.
00001〜100重量%であって、好ましくは0.0
01〜5重量%である。The usage concentration of the composite fungicidal and insecticide of the present invention is, for example, 0.
00001 to 100% by weight, preferably 0.0%
01 to 5% by weight.
本発明の複合殺菌殺虫剤は、使用形態に適合した通常の
方法で使用することができる。The composite fungicidal and insecticide of the present invention can be used in a conventional manner suitable for the usage form.
そして、式(I)の活性化合物と公知殺虫性化合物を、
実際の使用場面に際し、夫々を混合使用することができ
る、いわゆるタンクミックス(Tank■ix )の可
能な製剤形態で使用することも包含する。and the active compound of formula (I) and a known insecticidal compound,
In actual usage situations, it is also possible to use them in the form of a so-called tank mix, in which they can be used in combination.
本発明の内容を、実施例により具体的に説明するが、本
発明はこれらのみに限定されるべきものではない。The content of the present invention will be specifically explained with reference to examples, but the present invention should not be limited only to these examples.
生物試験ニー
供試化合物
1.1 :N−(1−(4−クロロフェニル)−エチ
ル)−2,2−ジクロロ−L3,3−トリメチルシクロ
プロパンカルボキサ
ミド
1.2 :N−(1−(4−クロロフェニル)−エチ
ル) −2,2−ジクロロ−1−エチル−3−メチルシ
クロプロパンカルボ
キサミド
1.3 :N−(1−(4−クロロフェニル)−エチ
ル)−2,2−ジクロロ−1−イソプロピルシクロプロ
パンカルボキサミ
ド
1.4 :N−(R)−(1−(4−クロロフェニル
)−エチル)−2,2−ジクロロ−1−エチル−3t−
メチル−1r−シ
クロプロパンカルボキサミドのジアス
テレオマー類の混合物
1.5 :N−(R)−(1−(4−クロロフエニル
)−エチル) −(I S) −2,2−ジクロロ−1
−エチル−3t−メチル
−1r−シクロプロパンカルボキサミ
ド
1.6 :N−(1−(4−ブロモフェニル)−エチ
ノL;)−2,2−ジクロロ−L3,3−トリメチルシ
クロプロパンカルボキサ
ミド
1.7 :N−(R)−(1−(4−クロロフェニル
)−エチル:l−2,2−ジクロロ−1−イソプロピル
シクロプロパン力ル
ポキサミドのジアステレオマー類の混
合物
A:O,O−ジメチル 0−4−メチルチt−m−)リ
ルホスホロチオエート
(−船名:フェンチオン)
B:S−α−エトキシカルボニルベンジル0.0−ジメ
チルホスホロジチオエー
ト (−船名:フェントエート)
C: (Z)−2−クロロ−1−(2,4,5−トリク
ロロフェニル)ビニル ジメチ
ルホスフェート
(−船名:テトラクロルビンホス)
D:O,O−ジメチル ○−3,5,6−)ジクロロ−
2−ピリジルホスホロチオエ
ート
(−船名:クロロピリホスメチル)
E:2.3−ジヒドロ−3−オキソ−2−フェニル−6
−ピリダジニル ジエチル
ホスホロチオネート
(−船名:ピリダフェンチオン)
F:O,O−ジエチル 0−2−iso−プロピル−6
−メチルピリミジン−4−
イルホスホロチオエート
(−船名:ダイアジノン)
実施例1
供試化合物の調製
活性化合物:5〜25重量部
担体:珪藻土とカオリンとの混合物(1:5)70重量
部〜90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
5重量部
上述した量の活性化合物、担体および乳化剤を粉砕混合
して各水和剤とし、その所定薬量を水で希釈して混合し
て調製する。Biological test compound 1.1: N-(1-(4-chlorophenyl)-ethyl)-2,2-dichloro-L3,3-trimethylcyclopropanecarboxamide 1.2: N-(1-(4- chlorophenyl)-ethyl) -2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamide 1.3: N-(1-(4-chlorophenyl)-ethyl)-2,2-dichloro-1-isopropylcyclo Propanecarboxamide 1.4: N-(R)-(1-(4-chlorophenyl)-ethyl)-2,2-dichloro-1-ethyl-3t-
Mixture of diastereomers of methyl-1r-cyclopropanecarboxamide 1.5: N-(R)-(1-(4-chlorophenyl)-ethyl)-(IS)-2,2-dichloro-1
-Ethyl-3t-methyl-1r-cyclopropanecarboxamide 1.6: N-(1-(4-bromophenyl)-ethino L;)-2,2-dichloro-L3,3-trimethylcyclopropanecarboxamide 1.7 : N-(R)-(1-(4-chlorophenyl)-ethyl: l-2,2-dichloro-1-isopropylcyclopropane Mixture of diastereomers of lupoxamide A: O,O-dimethyl 0-4 -Methylthi t-m-)lyl phosphorothioate (-ship name: fenthion) B: S-α-ethoxycarbonylbenzyl 0.0-dimethylphosphorodithioate (-ship name: fentoate) C: (Z)-2-chloro -1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate (-ship name: tetrachlorvinphos) D:O,O-dimethyl ○-3,5,6-)dichloro-
2-Pyridylphosphorothioate (-ship name: chloropyrifosmethyl) E: 2.3-dihydro-3-oxo-2-phenyl-6
-Pyridazinyl diethyl phosphorothionate (-ship name: pyridafenthione) F:O,O-diethyl 0-2-iso-propyl-6
-Methylpyrimidine-4-ylphosphorothioate (-Ship name: Diazinon) Example 1 Preparation of test compound Active compound: 5 to 25 parts by weight Support: 70 to 90 parts by weight of a mixture of diatomaceous earth and kaolin (1:5) Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenyl ether The above-mentioned amounts of the active compound, carrier and emulsifier are pulverized and mixed to form each wettable powder, which is prepared by diluting and mixing a predetermined amount with water.
水面施用効力試験
試験方法
水稲(品種:朝日)を直径12C1の白磁ポットに3株
植えて温水栽培し、その分けつ初期に予め調製した所定
濃度の薬液ピペットを用いて、直接稲体地上部にかから
ないように、表示薬量になるように、水面に潅注した。Water surface application efficacy test Test method Three paddy rice plants (variety: Asahi) are planted in white porcelain pots with a diameter of 12C1 and cultivated in warm water, and at the early stage of tillering, using a pipette with a pre-prepared medicinal solution at a predetermined concentration, do not directly apply it to the above-ground parts of the rice plant. The water surface was irrigated at the indicated dose.
その3日後、網籠をかけツマグロヨコバイ成虫を1ポッ
ト当り30頭接種し、接種2日後に死生を数え殺虫率を
算出した。Three days later, each pot was covered with a net cage and inoculated with 30 adult leafhoppers per pot, and two days after inoculation, dead and alive were counted to calculate the insecticidal rate.
又、薬剤処理20日後、常法によりイネいもち病菌胞子
の懸濁液を噴霧接種し、温度23〜25°C1相対湿度
100%の接種室内に24時間保った。Further, 20 days after the chemical treatment, a suspension of rice blast fungus spores was spray inoculated by a conventional method and kept in an inoculation chamber at a temperature of 23 to 25° C. and a relative humidity of 100% for 24 hours.
その後、温度20〜28°Cのガラス温室に移し、接種
7日後、鉢当りの罹病程度を下記の基準により類別評価
し、更に防除価(%)を求めた。また薬害も同様に調査
した。Thereafter, they were transferred to a glass greenhouse at a temperature of 20 to 28°C, and 7 days after inoculation, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. Drug damage was also investigated in the same way.
一■員度−A0
0.5 2未満
1 2〜5未満
2 5〜10未満
3 10〜20未満
4 20〜40未満
5 40以上
本試験は1区3鉢の結果である。その結果を第1表に示
す。Membership degree - A0 0.5 Less than 2 1 2 to less than 5 2 5 to less than 10 3 10 to less than 20 4 20 to less than 40 5 40 or more This test is the result of 3 pots in 1 section. The results are shown in Table 1.
第1表
実施例2
茎葉散布効力試験
(i)トビイロウンカ及びコブノメイガに対する試験
供試化合物の調製
各活性化合物:30〜40重量部
担体:珪藻土とカオリンとの混合物(1:5)55〜6
5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
5重量部
上述した量の活性化合物、担体および乳化剤を粉砕混合
して各水和剤とし、その所定薬量を水で希釈して混合し
て調製する。Table 1 Example 2 Efficacy test for foliage spraying (i) Preparation of test compounds against brown planthopper and brown borer moth Each active compound: 30 to 40 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5) 55 to 6
5 parts by weight Emulsifier: 5 parts by weight polyoxyethylene alkyl phenyl ether Each wettable powder is prepared by grinding and mixing the above-mentioned amounts of the active compound, carrier and emulsifier, diluting the prescribed amount with water and mixing. .
試験方法:
直径約13CI+のポットに草丈約15C11の稲を3
本植え、定植10日後に予め、調製した活性化合物の所
定濃度の水希釈液をスプレーガンを用いてlポット当り
20d散布し、散布薬液を風乾後ポットに網籠をかけ、
トビイロウンカ4令幼虫及びコブノメイガ4令幼虫を1
ポット当り夫々10接接種し、3日後に先主を数え殺虫
率を算出した。Test method: 3 rice plants with a plant height of about 15C11 in a pot with a diameter of about 13CI+
Main planting, 10 days after planting, a pre-prepared active compound diluted with water at a predetermined concentration was sprayed at 20 d per pot using a spray gun, and after air-drying the sprayed chemical solution, the pots were covered with a mesh basket.
4th instar larva of brown planthopper and 4th instar larva of brown borer moth
Ten inoculations were made per pot, and three days later, the insect kill rate was calculated by counting the number of insects.
(ii)イネいもち病に対する茎葉散布効力試験試験方
法
水稲(品種:朝日)を直径12C1の素焼鉢に栽培し、
その3〜4葉期に予め調製した活性化合物の所定濃度希
釈液を3鉢当り50m散布した。翌日人工培養したイネ
いもち病菌胞子の懸濁液を噴霧接種(2回)し、25℃
、相対湿度100%の温室に保ち感染せしめた。接種7
日後、鉢当りの罹病程度を下記の基準により類別評価し
、更に防除価(%)を求めた。また薬害も同時に調査し
た11Mw Ao
0.5 2未満
1 2〜5未満
2 5〜10未満
3 10〜20未満
4 20〜40未満
5 40以上
本試験は1区3鉢の結果である。(ii) Test method for foliar spray efficacy against rice blast disease Paddy rice (variety: Asahi) was grown in a clay pot with a diameter of 12C1,
At the 3rd to 4th leaf stage, a pre-prepared diluted solution of the active compound at a predetermined concentration was sprayed over 50 m per 3 pots. The next day, a suspension of artificially cultured rice blast fungus spores was spray inoculated (twice), and the temperature was increased to 25°C.
The cells were kept in a greenhouse at 100% relative humidity and infected. Inoculation 7
After a day, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. In addition, chemical damage was also investigated at the same time. 11 Mw Ao 0.5 Less than 2 1 2 to less than 5 2 5 to less than 10 3 10 to less than 20 4 20 to less than 40 5 40 or more This test is the result of 3 pots in 1 section.
前記試験(i)及び(ii)の結果をとりまとめ第2表
に示す。The results of the tests (i) and (ii) are summarized and shown in Table 2.
Claims (2)
体と、 O,O−ジメチルO−4−メチルチオ−m−トリルホス
ホロチオエート、 O,O−ジメチルO−4−ニトロ−m−トリルホスホロ
チオエート、 4−(メチルチオ)フェニルジプロピルホスフェート、 O−エチルO−4−ニトロフェニルフェニルホスホノチ
オエート、 O,O−ジメチルS−2−エチルチオエチルホスホロジ
チオエート、 S−α−エトキシカルボニルベンジルO,O−ジメチル
ホスホロジチオエート、 S−1,2−ビス(エトキシカルボニル)エチルO,O
−ジメチルホスホロチオエート、O,O−ジメチルS−
メチルカルバモイルメチルホスホロジチオエート、 O,O−ジメチルS−2−(1−メチルカルバモイルエ
チルチオ)エチルホスホロチオエート、 ジメチル2,2,2−トリクロロ−1−ヒドロキシエチ
ルホスホネート、 1,2−ジブロモ−2,2−ジクロロエチルジメチルホ
スフェート、 2,2−ジクロロビニルジメチルホスフェート、 2−クロロ−1−(2,4−ジクロロフェニル)ビニル
ジエチルホスフェート、 (Z)−2−クロロ−1−(2,4,5−トリクロロフ
ェニル)ビニルジメチルホスフェート、 ジメチル(E)−1−メチル−2−(メチルカルバモイ
ル)ビニルホスフェート、 O,O−ジメチルO−3,5,6−トリクロロ−2−ピ
リジルホスホロチオエート、 O−2−ジエチルアミノ−6−メチルピリミジン−4−
イルO,O−ジメチルホスホロチオエート、 O,O−ジエチルO−2−iso−プロピル−6−メチ
ルピリミジン−4−イルホスホロチオエート、 O,O−ジエチルO−2,3−ジヒドロ−3−オキソ−
2−フェニル−6−ピリダジニルホスホロチオエート、 O,O−ジエチルO−5−フェニルイソキサゾール−3
−イルホスホロチオエート、 S−2,3−ジヒドロ−5−メトキシ−2−オキソ−1
,3,4−チアジアゾール−3−イルメチルO,O−ジ
メチルホスホロジチオエート、 2−メトキシ−4H−1,3,2λ^5−ベンゾジオキ
サホスホリン−2−サルファイド、及びO−〔1−(4
−クロロフェニル)−1H−ピラゾール−4−イル〕O
−エチルS−プロピルホスホロチオエート より成る公知殺虫性化合物群から選ばれる一種とを有効
成分として含有することを特徴とする複合殺菌殺虫剤。(1) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, Z represents a halogen atom, R^1 represents an alkyl group having 1 to 4 carbon atoms, and R^2 represents a hydrogen atom, a methyl group, or ethyl group, and R^3 represents a hydrogen atom or a methyl group, and bactericidal carboxamides or optical isomers thereof, O,O-dimethyl O-4-methylthio-m-tolylphosphorothioate, O, O-dimethyl O-4-nitro-m-tolylphosphorothioate, 4-(methylthio)phenyldipropylphosphate, O-ethyl O-4-nitrophenylphenylphosphonothioate, O,O-dimethyl S-2-ethylthioethyl Phosphorodithioate, S-α-ethoxycarbonylbenzyl O,O-dimethylphosphorodithioate, S-1,2-bis(ethoxycarbonyl)ethyl O,O
-dimethyl phosphorothioate, O,O-dimethyl S-
Methylcarbamoylmethylphosphorodithioate, O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethylphosphorothioate, Dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate, 1,2-dibromo-2 ,2-dichloroethyldimethylphosphate, 2,2-dichlorovinyldimethylphosphate, 2-chloro-1-(2,4-dichlorophenyl)vinyldiethylphosphate, (Z)-2-chloro-1-(2,4,5 -trichlorophenyl)vinyldimethylphosphate, dimethyl(E)-1-methyl-2-(methylcarbamoyl)vinylphosphate, O,O-dimethyl O-3,5,6-trichloro-2-pyridylphosphorothioate, O-2- diethylamino-6-methylpyrimidine-4-
yl O,O-dimethyl phosphorothioate, O,O-diethyl O-2-iso-propyl-6-methylpyrimidin-4-yl phosphorothioate, O,O-diethyl O-2,3-dihydro-3-oxo-
2-phenyl-6-pyridazinyl phosphorothioate, O,O-diethyl O-5-phenylisoxazole-3
-ylphosphorothioate, S-2,3-dihydro-5-methoxy-2-oxo-1
, 3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorodithioate, 2-methoxy-4H-1,3,2λ^5-benzodioxaphosphorine-2-sulfide, and O-[1- (4
-chlorophenyl)-1H-pyrazol-4-yl]O
A composite fungicidal and insecticide comprising, as an active ingredient, one selected from the group of known insecticidal compounds consisting of -ethyl S-propyl phosphorothioate.
−ジクロロ−1,3,3−トリメチルシクロプロパンカ
ルボキサミド、 N−〔1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1,3,3−トリメチルシクロプロパンカ
ルボキサミド、 N−〔1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1−エチル−3−メチルシクロプロパンカ
ルボキサミド、 N−〔1−(4−クロロフェニル)−エチル〕−2,2
−ジクロロ−1−イソプロピルシクロプロパンカルボキ
サミド、 N−(R)−〔1−(4−クロロフェニル)−エチル〕
−2,2−ジクロロ−1−エチル−3t−メチル−1r
−シクロプロパンカルボキサミドのジアステレオマー類
の混合物、N−(R)−〔1−(4−クロロフェニル)
−エチル〕−2,2−ジクロロ−1−イソプロピルシク
ロプロパンカルボキサミドのジアステレオマー類の混合
物、 N−(R)−〔1−(4−クロロフェニル)−エチル〕
−(1S)−2,2−ジクロロ−1−エチル−3t−メ
チル−1r−シクロプロパンカルボキサミド、及び N−(R)−〔1−(4−クロロフェニル)−エチル〕
−(1S)−2,2−ジクロロ−1−イソプロピルシク
ロプロパンカルボキサミド より選ばれる一種である請求項(1)の複合殺菌殺虫剤
。(2) The fungicidal carboxamide or its optical isomer is N-[1-(4-promophenyl)-ethyl]-2,2
-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N-[1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N-[1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1-ethyl-3-methylcyclopropanecarboxamide, N-[1-(4-chlorophenyl)-ethyl]-2,2
-dichloro-1-isopropylcyclopropanecarboxamide, N-(R)-[1-(4-chlorophenyl)-ethyl]
-2,2-dichloro-1-ethyl-3t-methyl-1r
- mixture of diastereomers of cyclopropanecarboxamide, N-(R)-[1-(4-chlorophenyl)
-ethyl]-2,2-dichloro-1-isopropylcyclopropanecarboxamide mixture of diastereomers, N-(R)-[1-(4-chlorophenyl)-ethyl]
-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide, and N-(R)-[1-(4-chlorophenyl)-ethyl]
-(1S)-2,2-dichloro-1-isopropylcyclopropanecarboxamide The composite fungicidal and insecticide of claim (1).
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2276557A JPH04154707A (en) | 1990-10-17 | 1990-10-17 | Complex antimicrobial insecticide |
TW080107420A TW215895B (en) | 1990-10-17 | 1991-09-19 | |
KR1019910018078A KR0168854B1 (en) | 1990-10-17 | 1991-10-15 | Mixed fungicidal and insecticidal composition |
CN91109563A CN1032040C (en) | 1990-10-17 | 1991-10-17 | Mixed fungicidal and insecticidal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2276557A JPH04154707A (en) | 1990-10-17 | 1990-10-17 | Complex antimicrobial insecticide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04154707A true JPH04154707A (en) | 1992-05-27 |
Family
ID=17571150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2276557A Pending JPH04154707A (en) | 1990-10-17 | 1990-10-17 | Complex antimicrobial insecticide |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPH04154707A (en) |
KR (1) | KR0168854B1 (en) |
CN (1) | CN1032040C (en) |
TW (1) | TW215895B (en) |
-
1990
- 1990-10-17 JP JP2276557A patent/JPH04154707A/en active Pending
-
1991
- 1991-09-19 TW TW080107420A patent/TW215895B/zh active
- 1991-10-15 KR KR1019910018078A patent/KR0168854B1/en not_active IP Right Cessation
- 1991-10-17 CN CN91109563A patent/CN1032040C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR0168854B1 (en) | 1999-01-15 |
TW215895B (en) | 1993-11-11 |
CN1060577A (en) | 1992-04-29 |
KR920007536A (en) | 1992-05-27 |
CN1032040C (en) | 1996-06-19 |
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