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公开(公告)号:JPH09165375A
公开(公告)日:1997-06-24
申请号:JP27727096
申请日:1996-09-26
发明人: ENDO YOSHINORI , FUJISHIMA HIROSHI , MURAI KEIZABURO , MIYATA TETSUJI , WAKISAKA SEIICHI , SASAMA YASUHIRO
IPC分类号: C07D231/18 , A01N43/56 , C07D401/04
摘要: PROBLEM TO BE SOLVED: To obtain a new pyrazole derivative having an excellent insecticidal activity against many agricultural insect pests, substantially not affecting mammalian, fishes and beneficial insects, and useful as an active ingredient for insecticidal compositions. SOLUTION: This compound is expressed by formula I [A is CH, N, a group of the formula: C-X (X is a halogen; R is H, a lower (halo)alkyl, benzyl, phenyl; R is R , a lower alkenyl; R is H, X, a lower alkyl, a lower haloalkylthio, phenyl, CN, NO2 , amino; R is X; R is a lower haloalkyl; R is H, a lower (halo)alkyl, benzyl; R and R are simultaneously not H; (l), (m) are each 0, 1; (n) is 0, 1, 2], for example, 3-(2,6-dichloro-4-trifluorophenyl)-1-methyl-5- methylsulfenylpyrazole. The compound of formula I [(m) is 0; R is the formula: R (R is H, a lower alkyl, phenyl)] is obtained by reacting a compound of formula II with a compound of the formula: (R )2 SO4 or R2 -X.
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公开(公告)号:JPH07324078A
公开(公告)日:1995-12-12
申请号:JP11540794
申请日:1994-05-27
发明人: ENDO YOSHINORI , TADA ISAO , MOTOKI MINORU , FUJISHIMA HIROSHI , NAKAGAWA HIROBUMI , YANASE DAISUKE
IPC分类号: C07D249/12 , A01N43/653
摘要: PURPOSE:To obtain the new compound, capable of manifesting controlling effects thereof in a small dose on important weeds in a paddy field, nontoxic to rice plants and useful as a herbicide for the paddy field. CONSTITUTION:This compound of formula I (R is methyl or ethyl; R is a lower alkyl or a lower alkenyl; R is a lower alkyl), e.g., 4-(3-allyl-4- isopropyloxy-2,5-dichlorophenyl)3-trifluoromethyl-1-methyl-1,2,4-triaz ol-5(1H)-one. The compound of formula I is obtained by reacting a compound of formula II with trifluoroacetic anhydride in an organic solvent such as toluene or carbon tetrachloride.
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公开(公告)号:JPH06329691A
公开(公告)日:1994-11-29
申请号:JP12103193
申请日:1993-05-24
发明人: TAKAO HISASHI , ENDO YOSHINORI , MIYATA TETSUJI , IZUMI SUSUMU , MURAI KEIZABURO
摘要: PURPOSE:To obtain a new pyrane derivative having strongly insecticidal, acaricidal and nematocidal activity and excellently controlling activity against various resistant insect pests having agricultural problems, comprising 3- phosphoryloxy-4H-pyran-4-one derivative. CONSTITUTION:A pyrane derivative of formula I (R is H or 1-4C alkyl; R is 1-6C alkyl, benzyl or methoxymethyl) (e.g. 2-methyl-5-methoxy-3-hydroxy-4H- pyran-4-one) is mixed with a compound of formula II (R is methyl or ethyl; R is 3-5C alkyl; X is halogen) (e.g. O-ethyl, S-n-propylphosphoric acid chloride) in the presence of triethylamine in dichloromethane at 0-5 deg.C, reacted at 10 deg.C for 1 hour, cleaned with an acid and an aqueous solution of alkali, the solvent is distilled away and silica gel column chromatography separation is carried out to give the objective new pyrane derivative of formula III useful as an insecticide, an acaricide and an nematocide, etc.
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公开(公告)号:JPH06116223A
公开(公告)日:1994-04-26
申请号:JP27066892
申请日:1992-10-09
发明人: MOTOKI MINORU , ENDO YOSHINORI
IPC分类号: A01N37/50 , C07C251/86
摘要: PURPOSE:To provide a new hydrazinoacetic acid derivative having highly powerful insecticidal activity against various insect pests for paddy rice, also having remarkable controlling effects on various resistant insect pests. CONSTITUTION:A hydrazinoacetic acid derivative of formula 1 (R is H or lower alkyl; R is H or methyl; R is lower alkyl; X is H, halogen, lower alkyl or lower alkoxy; (n) is 1 or 2), e.g. ethyl (2,2-benzylidene-1-methyl) hydrazinoacetate. The compound of the formula I can be obtained by reaction of a hydrazinoacetic acid compound of formula 2 with a carbonyl compound of formula 3 in the presence or absence of a catalyst.
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公开(公告)号:JPH0395162A
公开(公告)日:1991-04-19
申请号:JP23448089
申请日:1989-09-08
发明人: ENDO YOSHINORI
IPC分类号: C07D231/18 , A01N43/56
摘要: NEW MATERIAL:A pyrazole derivative expressed by formula I [R is H, lower alkyl, lower alkenyl, lower alkynyl, phenyl-lower alkyl or -CH(R )COOR (R and R are H or lower alkyl); R is H, halogen, lower alkyl, lower alkoxy-lower alkyl or phenoxy-lower alkyl; X is halogen; Ar is formula II (Y and Y are halogen; R is lower alkyl or lower alkynyl)]. EXAMPLE:5-Chloro-1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methoxyp yrazole. USE:Useful as a herbicide, effective against weeds, such as polygonum and mugwort and usable for agricultural products, such as soybean, corn, fruit tree and paddy rice. PREPARATION:A compound expressed by formula III is halogenated with a halogenating agent expressed by formula IV ((n) is 1 or 2) to afford the compound expressed by formula I.
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公开(公告)号:JPH1017548A
公开(公告)日:1998-01-20
申请号:JP17480096
申请日:1996-07-04
IPC分类号: C07D417/04 , A01N43/38 , A01N43/78 , A01N47/06 , A01N47/36 , C04B40/00 , C07D209/42
摘要: PROBLEM TO BE SOLVED: To obtain the subject compound shown by a specific formula, having such high germicidal effect as to be selectively high on agrochemical-resistant germs, and useful as an agricultural/horticultural germicide. SOLUTION: This compound is shown by formula I (R is H, hydroxyl, a 1-4C acyl, 1-4C acyloxy, or 1-4C alkoxy; R is a 1-4C alkyl; R is H, a 1-4C alkyl, 2-4C alkenyl, phenyl or cyano; R and R are each a 1-4C alkyl or halogen), e.g. ethyl-4-chloro-3,7-dimethylindole-2-carboxylate. This compound of formula I is obtained, pref., for example, by reaction of a phenylhydrazine of formula II with a compound of formula III in the presence of a catalyst such as boron trifluoride etherate to form a hydrazone form of formula IV which, in turn, is heated at 150-200 deg.C for 30min to 2h or so in a solvent in the presence of an acid catalyst such as a polyphosphoric acid.
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公开(公告)号:JPH09143014A
公开(公告)日:1997-06-03
申请号:JP30865795
申请日:1995-11-28
IPC分类号: A01N43/653
摘要: PROBLEM TO BE SOLVED: To obtain the above highly selective composition containing a specific 1,2,4-triazole derivative as an active ingredient, expressing excellent herbicidal activities against weeds in upland fields at extremely low doses, providing no chemical damage to agricultural crops. SOLUTION: This agent contains a benzofuran skeleton-having 1,2,4-triazole derivative of formula I (R , R are each H, methyl; R , R are each a halogen, a lower alkyl, a lower alkoxy, a lower haloalkyl, a lower haloalkoxy, cyano; R is methyl, ethyl; X is 0, S). The upland fields are preferably upland fields wherein soybeans, cotton or wheat and barley are cultured. The compound of formula I is preferably used at a dose of 10-100g/10 are. The compound of formula I is obtained, e.g. by reacting a (thio)semicarbazide compound of formula II with trifluoroacetic anhydride. Important weeds in the uplant fields are Amaranthus retroflexus, Echinochloa crus-galli, Corchorus capsularis, Rumex obtusifolius, Cyperus microiria, Arenaria serpyllifolia L., etc.
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公开(公告)号:JPH07188220A
公开(公告)日:1995-07-25
申请号:JP33543393
申请日:1993-12-28
发明人: ENDO YOSHINORI , TADA ISAO , MOTOKI MINORU , NAKAGAWA HIROBUMI , YANASE DAISUKE
IPC分类号: C07D405/04 , A01N43/653
摘要: PURPOSE:To obtain a new 4-phenyl-1,2,4-triazole derivative showing excellently controlling effect on important weeds in a paddy field, useful as an active ingredient for a herbicide having safety to rice plants. CONSTITUTION:This 4-phenyl-1,2,4-triazole derivative is represented by formula 2 (R is H or a lower alkyl; R is methyl or ethyl; X is S or O). The compound of formula 2, for example, is obtained by reacting a carbazide of formula 3 with trifluoroacetic anhydride. The carbazide of formula 3, for example, is obtained by reacting an aniline of formula 4 with phosgene or thiophosgene to give a (thio)cyanate of formula 5 and reacting the (thio)cyanate with hydrazine. Since this herbicide for a paddy field is completely harmless to rice plants and can selectively control gramineous and broad-leaved weeds including weeds of the genus Digitaria and Panicum except the genus Oryza of the family Gramineae, the herbicide is extremely effective for improving production of paddy rice plant and controlling harmful weeds in paddy fields.
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公开(公告)号:JPS6229593A
公开(公告)日:1987-02-07
申请号:JP16956885
申请日:1985-07-30
发明人: ENDO YOSHINORI , TAKAO HISASHI
IPC分类号: C07F9/24 , A01N57/32 , C07F9/59 , C07F9/6533 , C07F9/655 , C07F9/6558
摘要: NEW MATERIAL:A compound shown by the formula I [R1 is H or lower alkyl; R2 is lower alkyl, lower alkenyl, cycloalkyl, phenyl or benzyl, or R1 and R2 are linked to form piperazino or morpholino; R3 is lower alkyl, cycloalkyl or phenyl; R4 is H, lower alkyl, lower alkenyl, cycloalkyl or phenyl; R5 is H or (halogen-substituted) lower alkyl; Y is O or S]. EXAMPLE:3-(O-Methyl-N-methylamidophosphoryloxy)-gamma-pyrone shown by the formula II. USE:An agricultural and horticultural insecticide and acaricide. PREPARATION:A 3-hydroxy-gamma-pyrone shown by the formula III is reacted with a phosphoric acid halide shown by the formula IV (X is halogen).
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公开(公告)号:JPH09278731A
公开(公告)日:1997-10-28
申请号:JP11042396
申请日:1996-04-04
发明人: IWAMURA HAJIME , MIYOSHI HIDETO , ENDO YASUHIRO , MANABE HIROSHI , ENDO YOSHINORI , SAGAYAMA KAZUMI , KOMURA TOMOZO
IPC分类号: C07D295/12 , A01N37/48 , A01N41/10 , A01N41/12 , A01N43/40 , C07C231/02 , C07C235/64 , C07C255/58 , C07C317/40 , C07C323/42
摘要: PROBLEM TO BE SOLVED: To obtain the subject new derivative expressed by specific formula, having excellent germicidal activity and safety to crops, and useful as a plant disease injury controlling agent against e.g. Mastigomycotina such as Peronosporaceae. SOLUTION: This new compound is expressed by formula I [R is H, a 1-6C alkanoyl, an alkali (alkaline earth) metal cation, etc.; X is H, a 1-6C alkyl, a 1-6C haloalkyl, a 3-6C cycloalkyl, a 1-6C alkoxy or alkoxycarbonyl; (n) is 1-5], e.g. 4'-butoxycarbonyl-2-hydroxy-5-notrobenzanilide. The new compound is obtained, pref. for example, by reaction between 5-nitrosalicylic acid of formula II and an aniline compound of formula III in the presence of a condensation agent in an inert solvent followed by reaction of the resultant 5-nitrosalicylic acid anilide of formula IV with an acylating agent in the presence of an acid binding agent in an inert solvent or in the absence of solvent.
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