JPS61171462A - Aniline derivative, preparation thereof, and agricultural and horticultural fungicide containing said derivative as active component - Google Patents
Aniline derivative, preparation thereof, and agricultural and horticultural fungicide containing said derivative as active componentInfo
- Publication number
- JPS61171462A JPS61171462A JP29727185A JP29727185A JPS61171462A JP S61171462 A JPS61171462 A JP S61171462A JP 29727185 A JP29727185 A JP 29727185A JP 29727185 A JP29727185 A JP 29727185A JP S61171462 A JPS61171462 A JP S61171462A
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、新規なアニリン誘導体、その製造法およびそ
れを有効成分として含有する農園芸用殺菌剤に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel aniline derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.
浸透移行性殺菌剤□が作物病害防除に利用され始めてか
ら、薬剤耐性菌の問題が重大になりつつある。薬剤耐性
菌が蔓駕した圃場では、その薬剤に十分な効力を期待す
ることはできなくなる。このような薬剤としては、例え
ばベノミル〔メチル 1−(ブチルカルバモイル)ベン
ズイミダゾール−2−イルカ−バメート〕、フベリダゾ
ール〔2−(2−フリル)ベンズイミダゾール〕、チア
ベンダゾール〔2−チアゾール−4−イルベンズイ主ダ
ゾール〕、カルペンダジム〔メチル ベンズイミダゾー
ル−2−イルカ−バメート〕、チオファネートメチル〔
ジメチル 4.4−o−)ユニしン ビス(8−チオア
ロファネート)〕、チオファネート〔ジメチル 4.4
−o−フェニレン ビス(8−チオアロファネート)〕
等のベンズイミダゾール・チオファネート系殺菌剤、お
よびプロシ尤トン(N−(8’ 、5’−ジクロロフェ
ニル)−1゜2−ジメチルシクロプロパン−1,2−ジ
カルボキシイミド〕、イプロジオン(8−(8’、5’
−ジクロロフェニル)−N−イソプロピル−2゜4−ジ
オキソイミダゾリジン−1−カルボキサミド〕、ビンク
ロゾリン(8−1’、5’ −ジクロロフェニル)−
5−メチル−5−1’ニル−1,8−オキサゾリジン−
2,4−ジオン〕、ジクロシリナート〔エチル 8−(
8’、5’−ジクロロフェニル)−5−メチル−2,4
−ジオキソオキサゾリジン−5−カルボキシレート〕等
の環状イミド系殺菌剤が挙げられる。Since systemic fungicides have been used for crop disease control, the problem of drug-resistant bacteria has become increasingly important. In fields where drug-resistant bacteria are prevalent, it is no longer possible to expect the drugs to have sufficient efficacy. Examples of such drugs include benomyl [methyl 1-(butylcarbamoyl)benzimidazole-2-ylbamate], fuberidazole [2-(2-furyl)benzimidazole], and thiabendazole [2-thiazol-4-ylbenzimidazole]. dazole], carpendazim [methyl benzimidazole-2-ylbamate], thiophanate methyl [
dimethyl 4.4-o-)unisine bis(8-thioallophanate)], thiophanate [dimethyl 4.4
-o-phenylene bis(8-thioallophanate)]
benzimidazole/thiophanate fungicides such as, procyton (N-(8',5'-dichlorophenyl)-1゜2-dimethylcyclopropane-1,2-dicarboximide), iprodione (8-(8 ', 5'
-dichlorophenyl)-N-isopropyl-2゜4-dioxoimidazolidine-1-carboxamide], vinclozolin (8-1',5'-dichlorophenyl)-
5-methyl-5-1'yl-1,8-oxazolidine-
2,4-dione], dicrosilinate [ethyl 8-(
8',5'-dichlorophenyl)-5-methyl-2,4
-dioxoxazolidine-5-carboxylate] and the like.
本発明者らは、このような状況に鑑み、前述の薬剤耐性
菌に効力を有する化合物を開発すべく種々検討した結果
、一般式CI)
〔式中、XおよびYは同一または相異なり、低級アルキ
レン基または低級アルコキシ低級アルキレン基を表わす
。In view of this situation, the present inventors conducted various studies in order to develop a compound that is effective against the aforementioned drug-resistant bacteria. Represents an alkylene group or a lower alkoxy lower alkylene group.
kp l s mおよびnは同一または相異なり、0ま
たはlを表わす。kp l s m and n are the same or different and represent 0 or l.
R1はニトロ基、2−ニトロビニル基、アミノ基、イソ
チオシアナト基、低級アルキルアミノ基または一般式
%式%
−5O,−NH−R,あるいは−5−R,で示されるル
(0)p
基を表わす(ここで、A′およびA″は同一または相異
なり、酸素原子または硫黄原子を表わし、R2およびR
;は同一または相異なり、低級アルキル基、低級アルケ
ニル基、低級アルキニル基、低級ハロアルキル基または
低級アルコキシアルキル基を表わし、pは0.1または
2を表わす。)。R1 is a nitro group, a 2-nitrovinyl group, an amino group, an isothiocyanato group, a lower alkylamino group, or a ru(0)p group represented by the general formula % -5O, -NH-R, or -5-R. (Here, A' and A'' are the same or different and represent an oxygen atom or a sulfur atom, and R2 and R
; are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0.1 or 2. ).
Zは水素原子、水酸基、低級アルキル基、低級アルケニ
ル基、低級アルキニル基、低級アルコキシカルボニルア
ルキル基または一般式−C−R3あるいは−SR4で示
される基を表わす(ここで、R3は低級アルキル基、低
級シクロアルキル基またはフェニル基を表わし、R4は
低級アルキル基、フェニル基または低級アルコキシカル
ボニル基を表わす。)。Z represents a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a group represented by the general formula -C-R3 or -SR4 (where R3 is a lower alkyl group, (represents a lower cycloalkyl group or phenyl group, and R4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group).
Aは酸素原子または硫黄原子を表わす。A represents an oxygen atom or a sulfur atom.
Bは低級アルキル基、低級アルケニル基、低級シクロア
ルキル基、フェニル基または一般式−W−R,で示され
る置換基を表わす(ここで、Wは酸素原子または硫黄原
子を表わし、R11は低級アルキル基、低級アルケニル
基、低級アルキニル基、低級ハロアルケニル基、低級ハ
ロアルキニル基または低級シクロアルキル基を表わすか
、またはハロゲン原子で置換されていてもよいフェニル
基を表わすか、またはハロゲン原子、シアノ基、フェニ
ル基、低級シクロアルキル基あるいは低級アルコキシル
基のうち少なくとも一つの原子または基で置換されたア
ルキル基を表わす。)。〕で示されるアニリン誘導体を
見出し、本発明に至った。B represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or a substituent represented by the general formula -WR (where W represents an oxygen atom or a sulfur atom, and R11 represents a lower alkyl group). group, lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or a halogen atom, a cyano group , phenyl group, lower cycloalkyl group, or lower alkoxyl group, and represents an alkyl group substituted with at least one atom or group). ] was discovered, leading to the present invention.
一般式(1)で示される本発明化合物が強い殺菌効果を
示す薬剤耐性菌としては、例えば、リンゴのうどんこ病
菌(Podosphaera 1eoucotrich
a)、黒星病菌(Venturia 1naequal
is) 、ナシの黒星病菌(Venturia nas
hicola)、モニリア病菌(Scler−otin
ia mali)、カキの炭そ病菌(G loeosp
oriumkaki )、モモの灰層病菌(5cler
otinia cinerea )、黒星病菌(Cla
dosprium carpophilum)、ブド
ウの灰色かび病菌(Botrytis cinerga
) 、黒とり病菌(E 1sinoe ampel
1na)、晩腐病菌(Glomerellacingu
lata)、テンサイの褐斑病菌(Cercospor
abeticola )、ビーナツツの褐斑病菌(Ce
rcosporaarachidicola )、黒渋
病菌(Cercospora personata)、
オオムギのうどんこ病菌(Erysiphe gram
inis f。Examples of drug-resistant bacteria for which the compound of the present invention represented by general formula (1) exhibits a strong bactericidal effect include Podosphaera 1eoucotrich.
a), Venturia 1naequal
is), Venturia nas
hicola), Scler-otin
ia mali), oyster anthracnose fungus (G loeosp
oriumkaki), peach gray layer fungus (5cler
otinia cinerea), Cla
dosprium carpophilum), Botrytis cinerga
), E 1sinoe ampel
1na), late rot fungus (Glomerella
lata), sugar beet brown spot fungus (Cercospor
abeticola), peanut brown spot fungus (Ce
rcospora arachidicola), Cercospora personata,
Erysiphe gram
inis f.
sp、 hordei)、アイ・スポット病菌(Cer
cosporellaherpotichoides)
、紅色雪腐病菌(Fusariumnivale )
、コムギのうどんこ病菌(E rys i phegr
aminis f、 Spa tritici ) 、
キュウリのうどんこ病菌(S phaerotheca
ful 1g1nea )、つる枯病菌(Mycos
phaerel la melonis)、灰色かび病
菌(B otrytis cinerea )、黒星病
菌(Cladosporiumeca humuli)
、ホップの灰色カビ病菌(Botryt−is cin
erea )、タバコのうどんこ病菌(Erysip−
he cichoracearum )、バラの黒星病
@ (D 1ploca−rpon rosae )、
ミカンのそうか病菌(Elsinoefawcetii
)、青かび病菌(Penicillium itali
c−um)、緑かび病菌(Penicillium d
igitatum )などが挙げられる。sp, hordei), eye spot fungus (Cer.
cosporellaherpotichoides)
, Fusarium nivale
, wheat powdery mildew (E rys i phegr)
aminis f, Spa tritici),
Powdery mildew of cucumber (S phaerotheca)
ful 1g1nea), vine blight fungus (Mycos
phaerel la melonis), Botrytis cinerea, Cladosporiumeca humuli
, Botryt-is cin
area), tobacco powdery mildew (Erysip-
he cichoracearum), rose scab @ (D 1ploca-rpon rosae),
Elsinoefawcetii
), Penicillium itali
c-um), Penicillium d
gitatum), etc.
次に、一般式〔1〕で示される本発明化合物の製造法に
ついて詳しく説明する。Next, the method for producing the compound of the present invention represented by general formula [1] will be explained in detail.
製法(a):
本発明化合物は一般式CI)
〔式中、X、Y、に、l、m、n、R1およびZは前記
と同一の意味を表わす。〕
で示される化合物と、一般式
%式%
〔式中、AおよびBは前記と同一の意味を表わし、R6
はハロゲン原子を表わす。〕で示される化合物とを溶媒
中、必要に応じて塩基の存在下、通常θ〜150″Cに
て、反応させることにより製造することができる。溶媒
としては、例えば水、ベンゼン、トルエン、キシレン、
ジエチルエーテル、テトラヒドロフラン、ジオキサン、
クロロホルム、四塩化炭素、酢酸エチル、ピリジン、N
、N−ジメチルホルムアミド等が挙げられ、塩基として
は、例えばピリジン、トリエチルアミン、NlN−ジエ
チルアニリン、水素化ナトリウム、水酸化カリウム等が
挙げられる。必要に応じ、テトラ−n−ブチルアンモニ
ウムプロミドのような、相間移動触媒も用いることがで
きる。Production method (a): The compound of the present invention has the general formula CI) [wherein X, Y, l, m, n, R1 and Z have the same meanings as above. ] A compound represented by the general formula % formula % [wherein A and B represent the same meanings as above, and R6
represents a halogen atom. ] in a solvent, if necessary in the presence of a base, usually at θ to 150"C. Examples of solvents include water, benzene, toluene, xylene, etc. ,
diethyl ether, tetrahydrofuran, dioxane,
Chloroform, carbon tetrachloride, ethyl acetate, pyridine, N
, N-dimethylformamide, etc., and examples of the base include pyridine, triethylamine, NlN-diethylaniline, sodium hydride, potassium hydroxide, and the like. A phase transfer catalyst, such as tetra-n-butylammonium bromide, can also be used if desired.
一般式(1)において置換基2が水素原子を表わす場合
、本発明化合物は、一般式(1)〔式中、X、Y、に、
l、m、n、R1およびAは前記と同一の意味を表わす
。〕
で示されるフェニルイソシアネート誘導体と、一般式
%式%
〔式中、RIIおよびWは前記と同一の意味を表わす。When the substituent 2 represents a hydrogen atom in the general formula (1), the compound of the present invention is a compound of the general formula (1) [wherein X, Y,
1, m, n, R1 and A have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula % [wherein RII and W represent the same meanings as above].
〕
で示される化合物とを、無溶媒もしくは溶媒中、通常θ
〜50°Cにて反応させることにより、製造することが
できる。溶媒としては、例工ば、ベンゼン、トルエン、
キシレン、ジエチルエーテル、テトラヒドロフラン、ジ
オキサン、N、N−ジメチルホルムアミド、クロロホル
ム、四塩化炭素等があげられる。必要に応じて、トリエ
チルアミン1、N、N−ジエチルアニリン、1.4−ジ
アザビシクロC2,2,2)オクタン等の塩基を触媒と
して用いることができる。反応は通常10時間以内に完
結する。] The compound represented by is added without a solvent or in a solvent, usually at θ
It can be produced by reacting at ~50°C. Examples of solvents include benzene, toluene,
Examples include xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, and carbon tetrachloride. If necessary, a base such as triethylamine 1,N,N-diethylaniline or 1,4-diazabicycloC2,2,2)octane can be used as a catalyst. The reaction is usually completed within 10 hours.
なお、一般式〔夏〕で示されるフェニルイソシアネート
誘導体は、相当するアニリン誘導体とホスゲンまたはチ
オホスゲンとを、有機溶媒ll:ベンゼン、トルエン、
キシレン、酢酸エチル)中、通常50℃から還流温度に
て反応させることにより得ることができる。In addition, the phenyl isocyanate derivative represented by the general formula [summer] is prepared by combining the corresponding aniline derivative and phosgene or thiophosgene in an organic solvent such as benzene, toluene,
It can be obtained by reacting in xylene, ethyl acetate) at a temperature usually from 50°C to reflux.
反応は通常10時間以内に完結する。The reaction is usually completed within 10 hours.
製法(C)ニ
一般式CI)において、置換基2が水素原子でない場合
、本発明化合物は、一般式(ff)〔式中、X # Y
e k* l # ” m ” t Rt # Aおよ
びBは前記と同一の意味を表わす。〕
で示されるアニリン誘導体と、一般式(V)Z’−R,
(マ〕
〔式中、2′は低級アルキル基、低級アルケニル基、低
級アルキニル基、低級アルコキシカルボニルアルキル基
または一般式
わしくここで、R3は低級アルキル基、低級シクロアル
キル基またはフェニル基を表ね )し、R4は低級
アルキル基、フェニル基または低級アルコキシカルボニ
ル基を表わす。)、R7は脱離基を表わす。〕
で示される化合物とを、溶媒中、塩基を用いて、通常0
〜100℃にて反応させることにより製造することがで
きる。反応は通常12時間以内に完結する。ここで脱離
基とは、ハロゲン原子、メシルオキシ基またはトシルオ
キシ基を表わす。溶媒としては、例えばN。In the production method (C) (general formula CI), when the substituent 2 is not a hydrogen atom, the compound of the present invention can be prepared by the general formula (ff) [wherein, X # Y
e k * l # " m " t Rt # A and B represent the same meanings as above. ] An aniline derivative represented by the general formula (V) Z'-R,
(Ma) [In the formula, 2' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula, where R3 represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group. ), and R4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group. ), R7 represents a leaving group. ] The compound represented by
It can be produced by reacting at ~100°C. The reaction is usually completed within 12 hours. The leaving group here represents a halogen atom, mesyloxy group or tosyloxy group. Examples of the solvent include N.
N−ジメチルホルムアミド、ジメチルスルホキシド、ジ
エチルエーテル、テトラヒドロフラン等が挙げられ、塩
基としては、例えば水素化ナトリウム、水酸化カリウム
等が挙げられる。Examples of the base include N-dimethylformamide, dimethyl sulfoxide, diethyl ether, and tetrahydrofuran. Examples of the base include sodium hydride and potassium hydroxide.
涜
製造(d):
で表わされる基が同一であり、一般式
〔式中、A′、A″およびR1は前記と同じ意味を表わ
す。〕
で示される基である場合、本発明化合物は、一般式(V
l)
NH!
〔式中、x e y * k e l# mおよびnは
前記と同じ意味を表わす。〕
で示される化合物と一般式〔■〕
R,−R,(■〕
〔式中、R8はハロゲン原子を表わし、R,はれる置換
基を表わす(ここで、A’、A″およびR2は前記と同
一の意味を表わす。)。〕で示される化合物とを、製法
(a)と同様に反応させることにより得ることができる
。Production (d): When the groups represented by are the same and represented by the general formula [wherein A', A'' and R1 have the same meanings as above], the compound of the present invention is General formula (V
l) NH! [In the formula, x ey * ke l# m and n represent the same meanings as above. ] Compounds represented by the general formula [■] R, -R, (■) [In the formula, R8 represents a halogen atom, and R represents a substituent (herein, A', A'' and R2 are It can be obtained by reacting the compound represented by the formula (having the same meaning as above) in the same manner as in the production method (a).
なお、一般式(Vl)で示される化合物は一般式CVt
+
〔式中、x、Y、に、l2mおよびnは前記と同じ意味
を表わす。〕
で示される化合物を還元する仁とにより製造することが
できる。The compound represented by the general formula (Vl) has the general formula CVt
+ [In the formula, x, Y, l2m and n represent the same meanings as above. ] It can be produced by reducing the compound shown in the following.
反応は溶媒中(例えば、エタノール、酢酸エチル、ジオ
キサン)、触媒(例えば、二酸化白金、パラジウム炭素
)を用いて、通常1〜100 気圧の水素雰囲気下、1
0〜200℃にて行われる。この反応は、通常12時間
以内で完結する。The reaction is carried out in a solvent (e.g., ethanol, ethyl acetate, dioxane) and a catalyst (e.g., platinum dioxide, palladium on carbon) under a hydrogen atmosphere of usually 1 to 100 atm.
It is carried out at 0-200°C. This reaction is usually completed within 12 hours.
なお、化合物(9)は、文献J、 Chem、 Soc
、。In addition, compound (9) is described in Document J, Chem, Soc
,.
1981.2492に記載の方法により合成することが
できる。It can be synthesized by the method described in 1981.2492.
次に、本発明化合物の製造例を示す。Next, production examples of the compounds of the present invention will be shown.
製造例
6.8−ジアミノ−1,8−ベンゾジオキサン8.82
f、N、N−ジエチルアニリン6.0Ofおよびジオキ
サン6011/の混合物にクロロ蟻酸メチル8.18f
を、水冷下、6分間かけて滴下した。反応液を室温で1
2時間放置したのち、氷水に注ぎ、酢酸エチルで抽出し
た。有機層を水洗した後、無水硫酸マグネシウムで乾燥
し、減圧下に溶媒を留去した。Production example 6.8-diamino-1,8-benzodioxane 8.82
Methyl chloroformate 8.18f in a mixture of f,N,N-diethylaniline 6.0Of and dioxane 6011/
was added dropwise over 6 minutes under water cooling. The reaction solution was heated to 1 at room temperature.
After standing for 2 hours, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
得られた残渣を、トルエンと酢酸エチルの混合溶媒を用
いたシリカゲルカラムクロマトグラフィーにより精製し
、6.8−ビス(メトキシ全カルボニルアミノ)−1,
8−ベンゾジオキサン〔化合物番号(44))4.94
Fを得た。The obtained residue was purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate to obtain 6,8-bis(methoxyallcarbonylamino)-1,
8-Benzodioxane [Compound number (44)) 4.94
I got an F.
収率 87.6%
m @ p * 156.5〜157.5℃同様にし
て、 16−イ
ツプロポキシカルボニルアミノー8−メトキシカルボニ
ルアミノ−1,8−ベンゾジオキサン〔化合制御ft
42 > )m、 p、 159〜160.5°C
および6−ニトキシカルボニルアミノー8−メトキシカ
ルボニルアミノ−1,8−ベンゾジオキサン〔化合物番
号(4g))
m、p、 149〜150℃
を得た。Yield: 87.6% m @ p * 156.5-157.5°C In the same manner, 16-itupropoxycarbonylamino-8-methoxycarbonylamino-1,8-benzodioxane [Combination control ft
42>) m, p, 159-160.5°C
and 6-nitoxycarbonylamino-8-methoxycarbonylamino-1,8-benzodioxane [compound number (4g)) m, p, 149-150°C were obtained.
このようにして得られた本発明化合物を第1表に例示す
る。The compounds of the present invention thus obtained are illustrated in Table 1.
本発明化合物を農園芸用殺菌剤の有効成分として用いる
場合は、他の何らの成分も加えずそのままでもよいが、
通常は、固体担体、液体担体、界面活性剤その他の製剤
用補助剤と混合して、乳剤、水和剤、懸濁剤、粉剤、液
剤等に製剤して用いる。When the compound of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, it may be used as is without adding any other ingredients;
Usually, it is mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries to formulate an emulsion, a wettable powder, a suspension, a powder, a liquid, and the like.
これらの製剤には有効成分として本発明化合物を、重量
比で1〜95%、好ましくは2〜80%含有する。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 95%, preferably 2 to 80%.
固体担体としては、カオリンクレー、アッタパルジャイ
トクレー、ベントナイト、酸性白土、パイロフェライト
、タルク、珪藻土、方解石、′トウモロコシ穂軸粉、ク
ルミ殻粉、尿素、硫酸アンモニウム、合成含水酸化珪素
等の微粉末あるいは粒状物があげられ、液体担体として
は、キシレン、メチルナフタレン等の芳香族炭化水素類
、イソプロパツール、エチレングリコール、セロソルブ
等のアルコール類、アセトン、シクロヘキサノン、イソ
ホロン等のケトン類、大豆油、綿実油等の植物油、ジメ
チルスルホキシド、アセトニトリル、水等があげられる
。As solid carriers, fine powders such as kaolin clay, attapulgite clay, bentonite, acid clay, pyroferrite, talc, diatomaceous earth, calcite, 'corn cob powder, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, soybean oil, and cottonseed oil. Examples include vegetable oils such as, dimethyl sulfoxide, acetonitrile, water, etc.
乳化、分散、湿展等のために用いられる界面活性剤とし
ては、アルキル硫酸エステル塩、アルキル(アリール)
スルホン酸塩、ジアルキルスルホコハク酸塩、lリオキ
シエチレンアルキルアリールエーテルリン酸エステル塩
、ナフタレンスルホン酸ホルマリン縮金物等の陰イオン
界面活性剤、ポリオキシエチレンアルキルエーテル、ポ
リオキシエチレンポリオキシプロピレンブロックコホ0
リマー、ソルビタン脂肪酸エステル、ポリオキシエチレ
ンソルビタン脂肪酸エステル等の非イオン界面活性剤等
があげられる。Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, l-lyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block coho 0
Examples include nonionic surfactants such as reamer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester.
製剤用補助剤としては、リグニンスルホン酸塩、アルギ
ン酸塩、ポリビニルアルコール、アラビアガム、CMC
(カルボキシメチルセルロース)、PAP(酸性リン酸
イソプロピル)等があげられる。As formulation adjuvants, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC
(carboxymethylcellulose), PAP (isopropyl acid phosphate), and the like.
次に製剤例を示す。Examples of formulations are shown below.
製剤例1 粉 剤
本発明化合物(44) 2部、クレー88部およびタル
ク10部をよく粉砕混合して主剤含有量2%の粉剤を得
る。Formulation Example 1 Powder 2 parts of the compound of the present invention (44), 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder containing 2% of the main ingredient.
製剤例2 水和剤
本発明化合物(44) 80部、珪藻土45部、ホワイ
トカーボン20部、湿潤剤(ラウリル硫酸ソーダ)8部
および分散剤(リグニンスルホン酸カルシウム)2部を
よく粉砕混合して主剤含有量80%の水和剤を得る。Formulation Example 2 Wettable powder 80 parts of the compound of the present invention (44), 45 parts of diatomaceous earth, 20 parts of white carbon, 8 parts of a wetting agent (sodium lauryl sulfate) and 2 parts of a dispersing agent (calcium lignin sulfonate) were thoroughly ground and mixed. A hydrating agent with a base ingredient content of 80% is obtained.
製剤例8 水和剤
本発明化合物(44) 50部、珪藻±45部、湿潤剤
(アルキルベンゼンスルホン酸カルシウム)2.5部お
よび分散剤(リグニンスルホン酸カルシウム)2.6部
をよく粉砕混合して主剤含有量50%の水和剤を得る。Formulation Example 8 Wettable powder 50 parts of the compound of the present invention (44), ±45 parts of diatom, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and 2.6 parts of dispersing agent (calcium ligninsulfonate) were thoroughly ground and mixed. A hydrating agent having a base agent content of 50% is obtained.
製剤例4 乳 剤
本発明化合物(44) 10部、シクロヘキサノン80
部および乳化剤(ポリオキシエチレンアルキルアリルエ
ーテル)10部を混合して主剤含有量10%の乳剤を得
る。Formulation Example 4 Emulsion Compound of the present invention (44) 10 parts, cyclohexanone 80 parts
1 part and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) to obtain an emulsion with a base agent content of 10%.
上述のようにして得られた製剤の施用量は通常10アー
ルあたり10〜10(lである。The application rate of the preparation obtained as described above is usually 10 to 10 (l) per 10 are.
さらにその使用濃度は0.005〜0.5%の範囲が望
ましいが、これらの使用量、濃度は剤型、施用時期、方
法、場所、対象病害、対象作物等によっても異なるため
前記範囲に拘わる乙となく増減することは何ら差し支え
ない。Further, the concentration used is preferably in the range of 0.005 to 0.5%, but the amount and concentration used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., so it is not limited to the above range. There is no problem with increasing or decreasing the amount regardless of B.
さらに他の殺菌剤、除草剤、植物生長調節剤および殺虫
剤と混合して使用することができる。Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.
次に試験例をあげ、本発明化合物の農園芸用殺菌剤とし
ての有用性をさらに明らかにする。なお、対照化合物は
第2表の一般名で表示する。Next, test examples will be given to further clarify the usefulness of the compound of the present invention as an agricultural and horticultural fungicide. Note that the control compounds are indicated by the common names shown in Table 2.
忙
第 2 表
注(1) 市販除草剤 注(巧 市販殺菌剤試験例
1 キュウリうどんこ病防除効果90露l容のプラスチ
ック製ポットに砂壌土をつめ、キュウリ(品種:相撲半
白)を播種した。これを室温で8日間栽培し、子葉が展
開したキュウリ幼苗を得た。この幼苗に製剤例4に準じ
てwI4製した下記本発明化合物の乳剤および対照化合
物の水和剤の水希釈液を液滴が葉面に十分屋付着するま
で茎葉散布した。Table 2 Note (1) Commercial herbicide Note (Takumi Commercial fungicide test example 1 Cucumber powdery mildew control effect Fill a 90 liter plastic pot with sandy loam and sow cucumbers (variety: Sumo Hanshiro) This was cultivated at room temperature for 8 days to obtain cucumber seedlings with expanded cotyledons.These seedlings were treated with an aqueous dilution of the following emulsion of the present compound and a hydrating powder of a control compound prepared wI4 according to Formulation Example 4. was sprayed on the foliage until enough droplets adhered to the leaf surface.
薬液風乾後、幼苗に薬剤耐性または感受性のキュウリう
どんこ病!i (Sphaerotheca fuli
gi−nea )の分生胞子懸濁液を噴霧接種した。こ
れを温室で10日間栽培し発病させた後、発病状態を観
察した。Chemical resistant or sensitive cucumber powdery mildew on young seedlings after air-drying the chemical solution! i (Sphaerotheca fuli)
gi-nea) was inoculated by spraying with a conidial suspension. After cultivating this in a greenhouse for 10 days to develop disease, the disease state was observed.
発病度は下記の方法によって算出した。The disease severity was calculated by the following method.
すなわち、調査葉の病斑出現に応じて、010.5.1
.2.4の指数に分類し、次式によって発病度を算出し
た。That is, depending on the appearance of lesions on the investigated leaves, on 010.5.1
.. The disease was classified into an index of 2.4, and the disease severity was calculated using the following formula.
(発病指数) (発病状態) O・・・・・葉面上にWIWlまたは病斑を認めない。(Incidence index) (Infection state) O: No WIWl or lesions observed on the leaf surface.
0.5・・・・・葉面上に葉面積の5%未満に菌叢また
は病斑を認める。0.5: Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area.
1・・・・・葉面上に葉面積の20%未満に菌叢または
病斑を認める。1: Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area.
2・・・・・葉面上に葉面積の50%未満に菌叢または
病斑を認める。2: Bacterial flora or lesions are observed on the leaf surface in less than 50% of the leaf area.
4・・・・・葉面上に葉面積の50%以上に菌叢または
病斑を認める。4...Bacterial flora or lesions are observed on the leaf surface over 50% or more of the leaf area.
つづいて防除価を次式より求めた。Next, the control value was calculated using the following formula.
その結果、第8表のように本発明化合物は薬剤耐性菌を
接種した場合優れた防除効果を示した。一方、市販殺菌
剤のベノミル、チオファネートメチル、カルペンダジム
のいずれも、薬剤耐性菌を接種した場合防除効果を示貯
さす、薬剤感受性菌接種した場合優れた防除 i効
果を示した。化学構造類似の市販除草剤はいずれの菌を
接種した場合もほとんど防除効果を示さなかった。As a result, as shown in Table 8, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria. On the other hand, the commercially available fungicides benomyl, thiophanate methyl, and carpendazim all showed excellent control effects when inoculated with drug-resistant bacteria, and showed excellent control effects when inoculated with drug-susceptible bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.
第 8 表
試験例2 テンサイ褐斑病防除効果
90g/容のプラスチック製ポットに砂壌土をつめ、テ
ンサイ(品種:デトロイトダークレッド)を播種した。Table 8 Test Example 2 Effect on controlling sugar beet brown spot disease A 90 g/volume plastic pot was filled with sandy loam, and sugar beet (variety: Detroit Dark Red) was sown.
温室で20日間栽培したのち得られた幼苗に、製剤例4
に準じて調製した下記本発明化合物の乳剤および対照化
合物の水和剤の水希釈液を液滴が葉面に十分付着するま
で茎葉散布した。薬液風乾後幼苗に薬剤耐性または感受
性のテンサイ褐斑病園(Cercospora bet
icola )の分生胞子懸濁液を噴霧接種した。これ
にビニールカバーをかぶせて多湿条件とし、温室でlO
日間栽培したのち、発病状態を観察した。発病調査方法
および防除価の算出は試験例1と同様に行った。Formulation Example 4 was applied to seedlings obtained after 20 days of cultivation in a greenhouse.
An emulsion of the compound of the present invention described below and a water-diluted solution of a hydrating powder of a control compound prepared according to the method described below were sprayed on foliage until the droplets sufficiently adhered to the leaf surface. After air-drying the chemical solution, the seedlings were exposed to chemically resistant or susceptible sugar beet brown spot (Cercospora bet).
icola) was inoculated by spraying with a conidial suspension. Cover this with a vinyl cover to create a humid condition, and place it in a greenhouse at 1000 ml.
After cultivation for one day, the disease state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.
その結果第4表のように試験例1の結果と同様に、本発
明化合物は薬剤耐性菌を接種した場合に優れた防除効果
を示し、逆に市販殺菌剤のベノミルおよびチオファネー
トメチル、カルペンダジムは薬剤感受性菌を接種した場
合に優れた防除効果を示した。化学構造類似の市販除草
剤はいずれの菌を接種した場合もほとんど防除効果を示
さなかった。As shown in Table 4, similar to the results of Test Example 1, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria, whereas the commercially available fungicides benomyl, thiophanate methyl, and carpendazim showed drug-resistant bacteria. It showed excellent control effect when inoculated with bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.
第 4 表
試験例8 ナシ黒星病防除効果
90g/容プラスチック製ポットにピートモスと砂壌土
の混合土壌をつめ、ナシの果実(品種:長十部)より採
取した種子を播いた。Table 4 Test Example 8 Pear scab control effect 90g/volume A plastic pot was filled with a mixed soil of peat moss and sandy loam, and seeds collected from pear fruit (variety: Chojube) were sown.
これを温室で20日間栽培し得られた幼苗に製剤例4に
準じて調製した下記本発明化合物の乳剤および下記対照
化合物の水和剤の水希釈液を液滴が葉面に十分付着する
まで茎葉散布した。薬液風乾後幼苗に薬剤耐性または感
受性のナシ黒星病菌(Venturia rrasbi
cola )の分生胞子懸濁液を噴霧接種した。これを
20°C多湿条件下に8日間置き、つづいて20℃蛍光
灯照明下に20日間栽培して発病させた。This was cultivated in a greenhouse for 20 days, and a water diluted solution of an emulsion of the compound of the present invention prepared according to Formulation Example 4 below and a hydrating powder of the control compound below was applied to the resulting seedlings until the droplets sufficiently adhered to the leaf surface. Sprayed on foliage. After air-drying the chemical solution, young seedlings were infected with drug-resistant or susceptible pear scab fungus (Venturia rrasbi).
cola) was inoculated by spraying with a conidial suspension. The plants were placed under humid conditions at 20°C for 8 days, and then cultivated under fluorescent lighting at 20°C for 20 days to develop the disease.
発病調査方法および防除価の算出は試験例1と同様にし
た。The disease onset investigation method and control value calculation were the same as in Test Example 1.
その結果、第5表のように本発明化合物は薬剤耐性菌を
接種した場合優れた防除効果を 1示し、逆に市
販殺菌剤のベノミルおよびチオファネートメチルは薬剤
感受性菌を接種した場合優れた防除効果を示した。As a result, as shown in Table 5, the compounds of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. Indicated.
第 6 表
試験例4 ビーナツツ褐斑病防除効果
100、gl容のプラスチック製ポットに砂壌土をつめ
、ビーナツツ(品種二千葉半立性)を播種した。温室で
14日間栽培したのち得られた幼苗に、製剤例4に準じ
て調製した下記本発明化合物の乳剤および下記対照化合
物の水和剤の水希釈液をポットあたり10xl茎葉散布
した。薬液風乾後、幼苗に薬剤耐性または感受性のビー
ナツツ褐斑病菌
(Cercospora arachidicola
)の胞子懸濁液を噴霧接種した。これにビニールカバー
をかぶせて多湿条件とし、温室で10日間栽培した後、
発病状態を観察した。発病調査方法および防除価の算出
は試験例1と崗様に行った。Table 6 Test Example 4 Peanut brown spot control effect A 100gl plastic pot was filled with sandy loam, and peanuts (variety: Nichiba semi-erect) were sown. After 14 days of cultivation in a greenhouse, the resulting seedlings were sprayed with 10xl per pot of a water diluted emulsion of the compound of the present invention prepared according to Formulation Example 4 and a hydrating powder of the control compound below. After the chemical solution is air-dried, the seedlings are infected with chemical-resistant or susceptible peanut brown spot fungus (Cercospora arachidicola).
) was inoculated by spraying with a spore suspension. After cultivating it in a greenhouse for 10 days under humid conditions by covering it with a vinyl cover,
The disease state was observed. The disease onset investigation method and control value calculation were carried out in the same manner as Test Example 1.
その結果、第6表のように本発明化合物は薬剤耐性菌を
接種した楊合優れた防除効果を示し、逆に市販殺菌剤の
ベノミルおよびチオファネートメチルは薬剤感受性菌を
接種した場合優れた防除効果を示した。As a result, as shown in Table 6, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. Indicated.
第 6 表
試験例6 キュウリ灰色カビ病防除効果90m容のプラ
スチック製ポットに砂壌土をつめ、キュウリ(品種:相
撲半白)をm種した。これを温室で8日間栽培し、子葉
が展開したキュウリを得た。この幼苗に製剤例4に準じ
て調製した本発明化合物の乳剤および下記対照化合物の
水和剤の水希釈液をポットあたり10g/!茎菜散布し
た。薬液風乾後、幼61に薬剤耐性ま1こは感受性のキ
ュウリ灰色カビ病菌(Botrytis cinere
a )のWi蝮切版(直径511m )を葉面上にはり
付けて接種しに。これを20℃多湿条件下に8日間量い
て発病させた後、発病状態を観察した。発病調査方法お
よび防除価の算出は試験例1と同様に行った。Table 6 Test Example 6 Cucumber gray mold control effect A 90 m capacity plastic pot was filled with sandy loam, and m types of cucumbers (variety: Sumo Hanshiro) were planted. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. To these seedlings, an emulsion of the compound of the present invention prepared according to Formulation Example 4 and a water diluted solution of a hydrating powder of the control compound below were added to the seedlings at 10 g/pot! Sprayed with stem vegetables. After air-drying the chemical solution, the cucumber gray mold fungus (Botrytis cinere
For inoculation by gluing the Wi cut version (diameter 511 m) of a) onto the leaf surface. This was weighed under humid conditions at 20° C. for 8 days to induce disease, and then the state of disease onset was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.
その結果、第7表のように本発明化合物は薬剤耐性菌を
接種した場合優れた防除効果を示し、逆Eζ市販殺=剤
のベノミルおよびチオファネートメチルは薬剤感受性菌
を接種した場合優れた防除効果を示した。As a result, as shown in Table 7, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria, and the commercially available inverse Eζ pesticides, benomyl and thiophanate methyl, showed excellent control effects when inoculated with drug-susceptible bacteria. Indicated.
第 7 表
試験例6 キュウリつる枯病防除効果
90sZ容のプラスチック製ポットに砂壌土をつめ、キ
ュウリ(品種:相撲半日)を播種した。これを温室で8
日間栽培し、子葉が展開したキュウリを得た。この幼苗
に製剤例4に準じて調製した下記本発明化合物の乳剤お
よび下記対照化合物の水和剤の水希釈液をポi[
ットあたり10TId茎葉散布した。薬液風乾後、幼苗
に薬剤耐性または感受性のキュウリつる枯病菌(Myc
osphaerella melonis ) cD菌
叢切版(直径5fll)を葉面上にはり付けて接種した
。Table 7 Test Example 6 Effect on controlling cucumber vine blight A plastic pot with a capacity of 90 sZ was filled with sandy loam, and cucumbers (variety: Sumo Half-day) were sown. 8 in a greenhouse
After cultivation for several days, cucumbers with expanded cotyledons were obtained. To these young seedlings, an emulsion of the following present compound prepared according to Formulation Example 4 and a water diluted solution of a hydrating powder of the following control compound were sprayed on the foliage at a rate of 10 TId per pot. After air-drying the chemical solution, seedlings are infected with drug-resistant or sensitive cucumber vine blight fungus (Myc).
osphaerella melonis) cD bacterial lawn cuttings (diameter 5 fl.) were pasted onto the leaf surface and inoculated.
これを20℃多湿条件下に8日間量いて発病させた後、
発病状態を観察した。発病調査方法および防除価の算出
は試験例1と同様に行った。After weighing this for 8 days under humid conditions at 20 degrees Celsius to induce disease,
The disease state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.
その結果、第8表のように本発明化合物は薬剤耐性菌を
接種した場合優れた防除効果を示し、逆に市販殺菌剤の
ベノミルおよびチオファネートメチルは薬剤感受性菌を
接種した場合優れた防除効果を示した。As a result, as shown in Table 8, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. Ta.
第 8 表
試験例7 tカン青かび病防除効果
ミカン果実(品種:温州)をよく水洗し、風乾した後、
製剤例4に準じて調製した下記本発明化合物の乳剤およ
び下記対照市販薬剤を水で希釈し所定濃度とした薬液に
1分間浸漬した。風乾後、薬剤耐性または感受性のミカ
ン青カビ病菌(Penicillium italic
um )分生胞子を水に懸濁し、果実表面に噴霧液温し
た。Table 8 Test Example 7 T-kan blue mold control effect After thoroughly washing tangerine fruit (variety: Unshu) with water and air drying,
The following emulsion of the present compound prepared according to Formulation Example 4 and the following control commercially available drug were diluted with water and immersed in a drug solution of a predetermined concentration for 1 minute. After air-drying, a drug-resistant or susceptible tangerine blue mold fungus (Penicillium italic)
um) Conidia were suspended in water and sprayed onto the fruit surface.
接種後14日間湿温室おいたのち、発病程度を下記のよ
う暑ζ0.1.2.8.4.6 の発病指数を用いて調
査した。 ゛
(発病状態 ) (発病指数)病斑が
認められない 0果実表面積の20%
未満に病斑が認められる#60〜80%’ //
4〃 80%以上に病斑が認められ
る 5発病度および防除価の算出は試験例1と
同様に行った。After inoculation, the seeds were kept in a humid room for 14 days, and then the severity of disease was investigated using the disease onset index of ζ0.1.2.8.4.6 as shown below. (Infection status) (Infection index) No lesions observed 0 20% of fruit surface area
Lesions are observed in less than #60-80%' //
4. Lesions are observed in 80% or more. 5. The disease severity and control value were calculated in the same manner as in Test Example 1.
その結果、第9表のように本発明化合物は薬剤耐性菌を
接種した場合優れた防除効果を示し、逆に市販殺菌剤の
ベノミルおよびチオノ1ネートメチルは薬剤感受性菌を
接種した場合優れた防除効果を示した。As a result, as shown in Table 9, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiono-1 nate-methyl showed excellent control effects when inoculated with drug-susceptible bacteria. showed that.
第 9 表
試験例8 作物に対する薬害試験
150g/容のプラスチック製ポットに砂壌土をつめ、
コムギ(品種:農林61号)、リンゴ(品種:紅玉)、
ビーチ1フ1品穏:千葉半立性)のそれぞれをL種し、
温室で栽培した。得られた幼苗に製剤例4に準じて調製
した下記本発明化合物の乳剤および下記対照化合物の水
和剤の水希釈液を茎葉散布した。Table 9 Test Example 8 Phytotoxicity test on crops A 150 g/volume plastic pot was filled with sandy loam,
Wheat (variety: Norin No. 61), apple (variety: Kogyoku),
Beach 1 F 1 item moderate: Chiba semi-erect) each L type,
Grown in a greenhouse. The obtained seedlings were sprayed with a water diluted emulsion of the compound of the present invention described below and a hydrating powder of the control compound described below, which were prepared according to Formulation Example 4.
散布後再び温室に置き、10日間栽培後、薬害発生の有
無を以下の基準により調査した。After spraying, the plants were placed in the greenhouse again, and after cultivation for 10 days, the presence or absence of phytotoxicity was investigated according to the following criteria.
薬害程度の基準 C程度) (症 状 )−異常なし。Standards for degree of drug damage Grade C) (Symptoms) - No abnormalities.
十 作物の一部に薬害による異常が認められる。10. Abnormalities due to chemical damage are observed in some of the crops.
什 作物の全体に薬害による異常が認められる。Abnormalities due to chemical damage are observed throughout the crop.
+薬害によって枯死となる。+Dying occurs due to chemical damage.
その結果、第10表から明らかなように、本発明化合物
には作物に対する薬害作用は認められず、対照に用いた
化学構造類似の市販除草剤に薬害作用が認められた。As a result, as is clear from Table 10, the compound of the present invention did not have a phytotoxic effect on crops, whereas a commercially available herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.
1゜1゜
Claims (6)
レン基または低級アルコキシ低級アルキレン基を表わす
。 k、l、mおよびnは同一または相異なり、0または1
を表わす。 R_1はニトロ基、2−ニトロビニル基、アミノ基、イ
ソチオシアナト基、低級アルキルアミノ基または一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 −NH−S−R_2、−O−S−R_2、−S−A′−
R_2、▲数式、化学式、表等があります▼、−SO_
2−A′−R_2、 −SO_2−NH−R_2あるいは−S−R_2で示さ
れる基を表わす(ここで、A′およびA″は同一または
相異なり、酸素原子または硫黄原子を表わし、R_2お
よびR′_2は同一または相異なり、低級アルキル基、
低級アルケニル基、低級アルキニル基、低級ハロアルキ
ル基または低級アルコキシアルキル基を表わし、pは0
、1または2を表わす。)。 Zは水素原子、水酸基、低級アルキル基、 低級アルケニル基、低級アルキニル基、低級アルコキシ
カルボニルアルキル基または一般式▲数式、化学式、表
等があります▼あるいは−SR_4で示される基を表わ
す(ここで、R_3は低級アルキル基、低級シクロアル
キル基またはフェニル基を表わし、R_4は低級アルキ
ル基、フェニル基または低級アルコキシカルボニル基を
表わす。)。 Aは酸素原子または硫黄原子を表わす。 Bは低級アルキル基、低級アルケニル基、 低級シクロアルキル基、フェニル基または一般式−W−
R_5で示される置換基を表わす(ここで、Wは酸素原
子または硫黄原子を表わし、R_5は低級アルキル基、
低級アルケニル基、低級アルキニル基、低級ハロアルケ
ニル基、低級ハロアルキニル基または低級シクロアルキ
ル基を表わすか、またはハロゲン原子で置換されていて
もよいフェニル基を表わすか、またはハロゲン原子、シ
アノ基、フェニル基、低級シクロアルキル基あるいは低
級アルコキシル基のうち少なくとも1つの原子または基
で置換されたアルキル基を表わす。)。〕 で示されるアニリン誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
2-A'-R_2, -SO_2-NH-R_2 or -S-R_2 (where A' and A'' are the same or different and represent an oxygen atom or a sulfur atom, and R_2 and R '_2 are the same or different, lower alkyl group,
Represents a lower alkenyl group, lower alkynyl group, lower haloalkyl group or lower alkoxyalkyl group, p is 0
, 1 or 2. ). Z represents a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a group represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ or -SR_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group or phenyl group, and R_4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group). A represents an oxygen atom or a sulfur atom. B is a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or the general formula -W-
Represents a substituent represented by R_5 (where W represents an oxygen atom or a sulfur atom, R_5 is a lower alkyl group,
Represents a lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, a cyano group, or a phenyl group. represents an alkyl group substituted with at least one atom or group of a group, a lower cycloalkyl group, or a lower alkoxyl group. ). ] Aniline derivative represented by.
レン基または低級アルコキシ低 級アルキレン基を表わす。 k、l、mおよびnは同一または相異なり、0または1
を表わす。 R_1はニトロ基、2−ニトロビニル基、アミノ基、イ
ソチオシアナト基、低級アルキ ルアミノ基または一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 −NH−S−R_2、−O−S−R_2、−S−A′−
R_2、▲数式、化学式、表等があります▼、−SO_
2−A′−R_2、 −SO_2−NH−R_2あるいは▲数式、化学式、表
等があります▼で示される基を表わす(ここで、A′お
よびA″は同一または相異なり、酸素原子または硫黄原 子を表わし、R_2およびR′_2は同一または相異な
り、低級アルキル基、低級アルケニル 基、低級アルキニル基、低級ハロアルキル 基または低級アルコキシアルキル基を表わ し、pは0、1または2を表わす。)。 Zは水素原子、水酸基、低級アルキル基、 低級アルケニル基、低級アルキニル基、低 級アルコキシカルボニルアルキル基または 一般式▲数式、化学式、表等があります▼あるいは−S
R_4で示される基を表わす(ここで、R_3は低級ア
ルキル基、低級シクロアルキル基またはフェニル基を 表わし、R_4は低級アルキル基、フェニル基または低
級アルコキシカルボニル基を表わ す。)。〕 で示される化合物と、一般式 ▲数式、化学式、表等があります▼ 〔式中、Aは酸素原子または硫黄原子を表 わす。Bは低級アルキル基、低級アルケニ ル基、低級シクロアルキル基、フェニル基 または一般式−W−R_5で示される置換基を表わす(
ここで、Wは酸素原子または硫黄 原子を表わし、R_5は低級アルキル基、低級アルケニ
ル基、低級アルキニル基、低級ハ ロアルケニル基、低級ハロアルキニル基ま たは低級シクロアルキル基を表わすか、ま たはハロゲン原子で置換されていてもよい フェニル基を表わすか、またはハロゲン原 子、シアノ基、フェニル基、低級シクロア ルキル基あるいは低級アルコキシル基のう ち少なくとも1つの原子または基で置換さ れたアルキル基を表わす。)。R_6はハロゲン原子を
表わす。〕 で示される化合物とを反応させることを特徴とする一般
式 ▲数式、化学式、表等があります▼ 〔式中、X、Y、k、l、m、n、R_1、Z、Aおよ
びBは前記と同じ意味を表わす。〕 で示されるアニリン誘導体の製造法。(2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.).Z is a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ or -S
Represents a group represented by R_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group, or phenyl group, and R_4 represents a lower alkyl group, phenyl group, or lower alkoxycarbonyl group). ] There are compounds represented by the general formula ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, A represents an oxygen atom or a sulfur atom. B represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or a substituent represented by the general formula -W-R_5 (
Here, W represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or is substituted with a halogen atom. or an alkyl group substituted with at least one atom or group selected from a halogen atom, a cyano group, a phenyl group, a lower cycloalkyl group, or a lower alkoxyl group. ). R_6 represents a halogen atom. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound shown by It has the same meaning as above. ] A method for producing an aniline derivative represented by
レン基または低級アルコキシ低 級アルキレン基を表わす。 k、l、mおよびnは同一または相異なり、0または1
を表わす。 R_1はニトロ基、2−ニトロビニル基、アミノ基、イ
ソチオシアナト基、低級アルキ ルアミノ基または一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 −NH−S−R_2、−O−S−R_2、−S−A′−
R_2、▲数式、化学式、表等があります▼、−SO_
2−A′−R_2、 −SO_2−NH−R_2あるいは▲数式、化学式、表
等があります▼で示される基を表わす(ここで、A′お
よびA″は同一または相異なり、酸素原子または硫黄原 子を表わし、R_2およびR′_2は同一または相異な
り、低級アルキル基、低級アルケニル 基、低級アルキニル基、低級ハロアルキル 基または低級アルコキシアルキル基を表わ し、pは0、1または2を表わす。)。 Aは酸素原子または硫黄原子を表わす。〕 で示されるフェニルイソシアネート誘導体と、一般式 R_5−W−H 〔式中、Wは酸素原子または硫黄原子を表 わし、R_5は低級アルキル基、低級アルケニル基、低
級アルキニル基、低級ハロアルケ ニル基、低級ハロアルキニル基または低級 シクロアルキル基を表わすか、またはハロ ゲン原子で置換されていてもよいフェニル 基を表わすか、またはハロゲン原子、シア ノ基、フェニル基、低級シクロアルキル基 あるいは低級アルコキシル基のうち少なく とも1つの原子または基で置換されたアル キル基を表わす。)。〕 で示される化合物とを、反応させることを特徴とする一
般式 ▲数式、化学式、表等があります▼ 〔式中、X、Y、k、l、m、n、R_1、A、Wおよ
びR_5は前記と同じ意味を表わす。〕 で示されるアニリン誘導体の製造法。(3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.) represents an oxygen atom or a sulfur atom.] A phenyl isocyanate derivative represented by the general formula R_5-W-H [wherein, W represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, a lower alkenyl group, a lower Represents an alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, a cyano group, a phenyl group, or a lower cycloalkyl group. (represents an alkyl group substituted with at least one atom or group among groups or lower alkoxyl groups).] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by ▼ [In the formula, X, Y, k, l, m, n, R_1, A, W and R_5 represent the same meanings as above.] A method for producing an aniline derivative represented by the following.
レン基または低級アルコキシ低 級アルキレン基を表わす。 k、l、mおよびnは同一または相異なり、0または1
を表わす。 R_1はニトロ基、2−ニトロビニル基、アミノ基、イ
ソチオシアナト基、低級アルキ ルアミノ基または一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 −NH−S−R_2、−O−S−R_2、−S−A′−
R_2、▲数式、化学式、表等があります▼、−SO_
2−A′−R_2、 −SO_2NH−R_2あるいは▲数式、化学式、表等
があります▼で示され基を表わす(ここで、A′および
A″は同一または相異なり、酸素原子または硫黄原子 を表わし、R_2およびR′_2は同一または相異なり
、低級アルキル基、低級アルケニル基、低級アルキニル
基、低級ハロアルキル基ま たは低級アルコキシアルキル基を表わし、 nは0、1または2を表わす。)。 Aは酸素原子または硫黄原子を表わす。Bは低級アルキ
ル基、低級アルケニル基、低級 シクロアルキル基、フェニル基または一般 式−W−R_5で示される置換基を表わす(ここで、W
は酸素原子または硫黄原子を表わ し、R_5は低級アルキル基、低級アルケニル基、低級
アルキニル基、低級ハロアルケニ ル基、低級ハロアルキニル基または低級シ クロアルキル基を表わすか、またはハロゲ ン原子で置換されていてもよいフェニル基 を表わすか、またはハロゲン原子、シアノ 基、フェニル基、低級シクロアルキル基あ るいは低級アルコキシル基のうち少なくと も1つの原子または基で置換されたアルキ ル基を表わす。)。〕 で示されるアニリン誘導体と、一般式 Z′−R_7 〔式中、Z′は低級アルキル基、低級アルケニル基、低
級アルキニル基、低級アルコキ シカルボニルアルキル基または一般式 ▲数式、化学式、表等があります▼あるいは−SR_4
で示される基を表わし(ここで、R_3は低級アルキル
基、低級シクロアルキル基またはフェニル基を表わし、
R_4は低級アルキル基、フェニル基または低級アルコ
キシカルボニル基を表わす。)、 R_7は脱離基を表わす。〕 で示される化合物とを、反応させることを特徴とする一
般式 ▲数式、化学式、表等があります▼ 〔式中、X、Y、k、l、m、n、R_1、Z′、Aお
よびBは前記と同一の意味を表わす。) で示されるアニリン誘導体の製造法。(4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
2-A'-R_2, -SO_2NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ to represent a group (here, A' and A'' are the same or different and represent an oxygen atom or a sulfur atom) , R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and n represents 0, 1 or 2.) A is oxygen. B represents a lower alkyl group, lower alkenyl group, lower cycloalkyl group, phenyl group, or a substituent represented by the general formula -W-R_5 (here, W
represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkyl group, or even if it is substituted with a halogen atom. It represents a phenyl group, or an alkyl group substituted with at least one atom or group selected from a halogen atom, a cyano group, a phenyl group, a lower cycloalkyl group, or a lower alkoxyl group. ). ] Aniline derivatives represented by the general formula Z'-R_7 [wherein Z' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula ▲ Numerical formula, chemical formula, table, etc. ▼Or-SR_4
represents a group represented by (where R_3 represents a lower alkyl group, lower cycloalkyl group or phenyl group,
R_4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group. ), R_7 represents a leaving group. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by B represents the same meaning as above. ) A method for producing the aniline derivative shown in
レン基または低級アルコキシ低 級アルキレン基を表わし、k、l、mおよびnは同一ま
たは相異なり、0または1を表 わす。〕 で示される化合物と、一般式 R_8−R_9 〔式中、R_8はハロゲン原子を表わし、R_9は一般
式▲数式、化学式、表等があります▼あるいは▲数式、
化学式、表等があります▼ で示される置換基を表わす(ここで、A′およびA″は
同一または相異なり、酸素原子または硫黄原子を表わし
、R_2は低級アルキル基、低級アルケニル基、低級ア
ルキニル基、低級ハロアルキル基または低級アルコキシ
ルアル キル基を表わす。)。〕 で示される化合物とを反応させることを特徴とする一般
式 ▲数式、化学式、表等があります▼ 〔式中、X、Y、k、l、m、nおよびR_9は前記と
同じ意味を表わす。〕 で示されるアニリン誘導体の製造法。(5) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group, and k, l, m and n are the same or Differently, they represent 0 or 1. ] A compound represented by the general formula R_8-R_9 [In the formula, R_8 represents a halogen atom, and R_9 is the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Numerical formulas,
There are chemical formulas, tables, etc. ▼ Represents a substituent shown by , represents a lower haloalkyl group or lower alkoxylalkyl group).] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by ▼ [In the formula, X, Y, k, l, m, n and R_9 have the same meanings as above.] A method for producing an aniline derivative represented by the following.
レン基または低級アルコキシ低 級アルキレン基を表わす。 k、l、mおよびnは同一又は相異なり、 0または1を表わす。 R_1はニトロ基、2−ニトロビニル基、アミノ基、イ
ソチオシアナト基、低級アルキ ルアミノ基または一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ −NH−S−R_2、−O−S−R_2、−S−A′−
R_2、▲数式、化学式、表等があります▼、−SO_
2−A′−R_2、 −SO_2−NH−R_2あるいは▲数式、化学式、表
等があります▼で示される基を表わす(ここで、A′お
よびA″は同一または相異なり、酸素原子または硫黄原 子を表わし、R_2およびR′_2は同一または相異な
り、低級アルキル基、低級アルケニル 基、低級アルキニル基、低級ハロアルキル 基または低級アルコキシアルキル基を表わ し、pは0、1または2を表わす。)。 Zは水素原子、水酸基、低級アルキル基、 低級アルケニル基、低級アルキニル基、低 級アルコキシカルボニルアルキル基または 一般式▲数式、化学式、表等があります▼あるいは−S
R_4で示される基を表わす(ここで、R_3は低級ア
ルキル基、低級シクロアルキル基またはフェニル基を わし、R_4は低級アルキル基、フェニル基または低級
アルコキシカルボニル基を表わす。)。 Aは酸素原子または硫黄原子を表わす。 Bは低級アルキル基、低級アルケニル基、 低級シクロアルキル基、フェニル基または 一般式−W−R_5で示される置換基を表わす(ここで
、Wは酸素原子または硫黄原子を 表わし、R_5は低級アルキル基、低級アルケニル基、
低級アルキニル基、低級ハロアル ケニル基、低級ハロアルキニル基または低 級シクロアルキル基を表わすか、またはハ ロゲン原子で置換されていてもよいフェニ ル基を表わすか、またはハロゲン原子、シ アノ基、フェニル基、低級シクロアルキル 基あるいは低級アルコキシル基のうち少な くとも1つの原子または基で置換されたア ルキル基を表わす。)。〕 で示されるアニリン誘導体を有効成分として含有するこ
とを特徴とする農園芸用殺菌剤。(6) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different and represent 0 or 1. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables etc.▼ -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.).Z is a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ or -S
Represents a group represented by R_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group, or phenyl group, and R_4 represents a lower alkyl group, phenyl group, or lower alkoxycarbonyl group). A represents an oxygen atom or a sulfur atom. B represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or a substituent represented by the general formula -W-R_5 (here, W represents an oxygen atom or a sulfur atom, and R_5 is a lower alkyl group) , lower alkenyl group,
Represents a lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, cyano group, phenyl group, lower cyclo It represents an alkyl group or a lower alkoxyl group substituted with at least one atom or group. ). ] An agricultural and horticultural fungicide characterized by containing an aniline derivative represented by the following as an active ingredient.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB08500022A GB2169283A (en) | 1985-01-02 | 1985-01-02 | Fungicidal aniline derivatives |
GB8500022 | 1985-01-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61171462A true JPS61171462A (en) | 1986-08-02 |
JPH0688955B2 JPH0688955B2 (en) | 1994-11-09 |
Family
ID=10572316
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP29727285A Pending JPS61165308A (en) | 1985-01-02 | 1985-12-27 | Fungicidal composition for agricultural and horticultural purposes |
JP29727185A Expired - Lifetime JPH0688955B2 (en) | 1985-01-02 | 1985-12-27 | Aniline derivative and agricultural and horticultural fungicide containing the same as an active ingredient |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP29727285A Pending JPS61165308A (en) | 1985-01-02 | 1985-12-27 | Fungicidal composition for agricultural and horticultural purposes |
Country Status (2)
Country | Link |
---|---|
JP (2) | JPS61165308A (en) |
GB (1) | GB2169283A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992012144A1 (en) * | 1990-12-28 | 1992-07-23 | Teijin Limited | Condensed benzoxa ring compound, production thereof, and pharmaceutical composition containing the same |
-
1985
- 1985-01-02 GB GB08500022A patent/GB2169283A/en active Pending
- 1985-12-27 JP JP29727285A patent/JPS61165308A/en active Pending
- 1985-12-27 JP JP29727185A patent/JPH0688955B2/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992012144A1 (en) * | 1990-12-28 | 1992-07-23 | Teijin Limited | Condensed benzoxa ring compound, production thereof, and pharmaceutical composition containing the same |
US5496853A (en) * | 1990-12-28 | 1996-03-05 | Teijin Limited | Benzoxa condensed ring compounds, process for producing the same and pharmaceutical composition comprising the same |
Also Published As
Publication number | Publication date |
---|---|
JPS61165308A (en) | 1986-07-26 |
GB2169283A (en) | 1986-07-09 |
GB8500022D0 (en) | 1985-02-13 |
JPH0688955B2 (en) | 1994-11-09 |
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