公开(公告)号：JPH04305628A

公开(公告)日：1992-10-28

申请号：JP9496091

申请日：1991-04-02

Applicant: AGENCY IND SCIENCE TECHN ,  TOKUYAMA SODA KK

Inventor： OKAMOTO HIDENORI ,  TANAKA NORIHIRO ,  KITAJIMA TOSHIO ,  FUKAYA TOSHIO

IPC: C07D275/06 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE:To obtain an organic compound having high nonlinear optical effect, consisting of a 2-nitrothiophene derivative shown in a specified expression. CONSTITUTION:This organic nonlinear optical material consists of a 2- nitrothiophene derivative shown in an expression I. In expression I, R is hydrogen atom or halogen atom. The 2-nitrothiophene derivative generates intensive secondary higher harmonics of green light (533nm) by being irradiated with ND:YAG laser(1064nm), etc. The 2-nitrothiophene derivative is a stable crystal and is used not only as a single crystal but also as a fiber or a vapor-deposited film and is usable compound as a nonlinear optical material for an optical wavelength conversion element, an optical switching element, etc.

公开(公告)号：JPH0625222A

公开(公告)日：1994-02-01

申请号：JP18503192

申请日：1992-07-13

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO

IPC: C07D333/40

Abstract: PURPOSE:To selectively produce a 3-hydroxy-2-thiophenecarboxylic acid derivative in a high yield by reacting a specified thioether derivative with an alkaline metal (bi) carbonate. CONSTITUTION:The objective compound of formula II, e.g. methyl 3-hydroxy-2- thiophenecarboxylate is obtsined by reacting a compound of formula I (R1 is a subatitutive alkyl of a substitutive phenyl; R2 is H, a halogen, a substitutive alkyl or a substitutive phenyl or NO2; R3 is an alkyl or phenyl; X is a halogen), e.g. methyl 2-chloro-3-methoxycarbonylmethylthiopropionate with a compound of the formula Y2CO3 (Y is Na, K or Li) or a compound of the formula YHCO3 at temperatures within a range of -70 to 150 deg.C, preferably -10 to 80 deg.C. By using an alkaline metal (bi) carbonate in place of an alkaline metal alcolate unlike in the conventional method, not only generation of impurities but decomposition of the product can be inhibited.

公开(公告)号：JPH0421677A

公开(公告)日：1992-01-24

申请号：JP12310790

申请日：1990-05-15

Applicant: TOKUYAMA SODA KK

Inventor： KITAJIMA TOSHIO ,  KATO SHOZO

IPC: C07D333/42 ,  A01N43/10

Abstract: NEW MATERIAL:A compound of formula I [X1 and X2 are each H, halogen, formyl, NO2, CN, alkoxy, alkylthio, (substituted)alkyl, etc.; X3 and X4 are each H, halogen or (substituted)alkyl; R is H, (substituted)alkyl or (substituted)phenyl; Y is NR R (R and R are each H, alkyl, alkenyl, etc.) or OR (R is H or alkyl)]. EXAMPLE:2-[p-(2-Nitro-3-thienyloxy)phenoxy]ethyl butyrate. USE:A bactericide/fungicide. PREPARATION:For example, the objective compound of the formula I can be obtained by a reaction, in the presence or absence of a solvent (e.g. benzene, toluene, xylene), between (A) a halogenothiophene compound of formula II (X5 is halogen) and (B) a phenol derivative of formula III (M is H or alkali metal).

公开(公告)号：JPH04279505A

公开(公告)日：1992-10-05

申请号：JP6367791

申请日：1991-03-06

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO ,  KOBUTANI TADASHI

IPC: A01N37/22 ,  A01N33/08 ,  A01N43/40

Abstract: PURPOSE:To obtain a herbicide composition exhibiting effective herbicidal effect at a low rate of application by combining a new phenylamine derivative with a chloroacetamide derivative. CONSTITUTION:The objective herbicide composition contains active components consisting of a combination of (A) a new phenylamine derivative of formula I [Z is =C(X3)-(X3 is H, halogen or alkyl) or N; X1 and X2 are H, halogen or alkyl; A is H, halogen, nitro, cyano or alkoxycarbonyl; R1 is alkoxyalkyl, alkenyloxyalkyl, alkynyloxyalkyl, phenoxyalkyl, furfuryl, etc.] [e.g. 4-(2',4'- dichlorophenoxy)-2-methoxyethylnitrobenzene] and (B) a chloroacetamide derivative of formula II (R2 and R3 are H or alkyl; R4 is alkoxyalkyl, alkenyloxyalkyl, etc.) (e.g. the compound of formula III). The composition can be used for the treatment of paddy soil and the effect can be developed at a low rate of application.

公开(公告)号：JPH0656820A

公开(公告)日：1994-03-01

申请号：JP20863992

申请日：1992-08-05

Applicant: TOKUYAMA SODA KK

Inventor： KITAJIMA TOSHIO ,  ISHIZAKI MASAHIKO

IPC: C07D333/32 ,  C07D333/38 ,  C07D333/42

Abstract: PURPOSE:To selectively produce a thienyl ether derivative in high yield by reacting a hydroxythiophene metal salt derivative with a halogeno compound. CONSTITUTION:A compound of formula I (A is an alkali metal; R is CN, alkoxycarbonyl, phenoxycarbonyl or aminocarbonyl; R is H, halogen, substitutable alkyl, substitutable phenyl, NO2, CN, alkoxycarbonyl, phenoxycarbonyl or aminocarbonyl) is made to react with a compound of the formula R X (X is a halogen; R is an alkyl, alkenyl or an alkynyl) in a molar ratio of the former:the latter of (1:1) to (1:100), preferably (1:1) to (1:20) at -70 to 200 deg.C, preferably -10 to 150 deg.C to provide the compound of formula II. According to this invention, the thienyl ether derivative can be obtained in a high yield even in an alcoholic organic solvent.

公开(公告)号：JPH04342505A

公开(公告)日：1992-11-30

申请号：JP11632591

申请日：1991-05-21

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO ,  KOBUTANI TADASHI

IPC: A01N33/22 ,  A01N37/18

Abstract: PURPOSE:To obtain a herbicide composition capable of synergistically enhancing weeding activity and having excellent weeding effect on a perennial weed such as Cyperus serotinus Rottb. or Sagittaria pygmaea Makino. difficult to weed when using each component individually by using a new phenylamine derivative in combination with a specific acetamide derivative. CONSTITUTION:(A) A new substance expressed by formula I [Z is formula II or N; X1 to X3 are H, halogen, haloalkyl or alkyl; A is halogen, NO3, CN or alkoxycarbonyl; R1 is substituted or unsubstituted (alkoxyalkyl, alkenyloxyalkyl or phenoxyalkyl), alkynyloxyalkyl, tetrahydrofurfuryl, furfuryl or thienylmethyl@{9147-28} is blended with (B) N-(1,1-dimethylbenzyl)-2-bromo-t- butylacetamide as active ingredients at an amount of the component B of 100-1000 pts.wt., preferably 100-500 pts.wt. based on 100 pts.wt. component A to provide a herbicide composition having excellent weeding effect on a perennial weed.

公开(公告)号：JPH04217647A

公开(公告)日：1992-08-07

申请号：JP41030090

申请日：1990-12-12

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO ,  KOBUTANI TADASHI ,  KATO TSUNEAKI

IPC: A01N33/10 ,  A01N43/36 ,  A01N43/40 ,  C07C217/90 ,  C07C229/56 ,  C07C255/59 ,  C07D213/30 ,  C07D307/52

Abstract: PURPOSE:To provide a new phenylamine derivative having high herbicidal activity, exhibiting highly selective herbicidal action especially against broad- leaved weeds and causing little phytotoxicity. CONSTITUTION:A compound of formula I [Z is group of formula II (X3 is H, halogen or alkyl) or N; X1 and X2 are H, halogen or alkyl; A is H, halogen, nitro, etc.; R is alkoxyalkyl, alkenyloxyalkyl, etc.], e.g. 4-(2',4'- dichlorophenoxy)-2-methoxyethylaminonitro-benzene. The compound can be produced by reacting a phenyl derivative of formula III (X4 is halogen or nitro) with an amine derivative of formula RNH2 in the presence or absence of a solvent (e.g. benzene) at -30 to +200 deg.C. The herbicide is effective against paddy field weeds such as barnyard grass and false pimpernel and plowed land weeds such as large crab-grass and green foxtail.

公开(公告)号：JPH03279382A

公开(公告)日：1991-12-10

申请号：JP7709390

申请日：1990-03-28

Applicant: TOKUYAMA SODA KK

Inventor： KITAJIMA TOSHIO ,  KATO SHOZO

IPC: C07D409/12 ,  A01N43/40 ,  A61K31/44 ,  A61K31/4433 ,  A61P17/00

Abstract: NEW MATERIAL:The compound of formula I [X1 to X5 are H, halogen, formyl, nitro, cyano, OH, alkoxy, alkylthio, monoalkylamino, (substituted) alkyl, (substituted) phenyl, etc.]. EXAMPLE:3-(3-Pyridyloxy)-2-nitrothiophene. USE:A bactericidal and fungicidal agent. PREPARATION:A halogenopyridine compound of formula II (X6 is halogen) is made to react with a hydroxythiophene compound of formula III in the presence of a hydrogen halide capturing agent optionally in a solvent.

公开(公告)号：JPH04342510A

公开(公告)日：1992-11-30

申请号：JP11632491

申请日：1991-05-21

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO ,  KOBUTANI TADASHI

IPC: A01N47/30 ,  A01N33/22

Abstract: PURPOSE:To obtain a herbicide composition having synergistically increased herbicidal activity by using both a new phenylamine derivative and a specific ures derivative and showing excellent herbicidal effects on perennial weeds such as Cyperus serotinus Rottb. and Sagittaria pygmaea MAKINO not to be weeded with each single component. CONSTITUTION:(A) A new substance shown by formula I [Z is group shown by formula II or N; X1 to X3 are H, halogen, alkyl or haloalkyl; A is H, halogen, NO2, CN or alkoxycarbonyl; R1 is substituted or nonsubstituted(alkoxyalkyl, alkenyloxyalkyl, phenoxyalkyl), alkynyloxyalkyl, tetrahydrofuryl, furfuryl or thienylmethyl] is blended with (B) a compound shown by formula III [R2 is substituted or nonsubstituted (phenyl or benzyl)] as active ingredients in a ratio of 100 pts.wt. component A and usually 100-1,000 pts.wt., preferably 400-700 pts.wt. component B to give a herbicide composition having the above-mentioned effects.

公开(公告)号：JPH04230278A

公开(公告)日：1992-08-19

申请号：JP40737290

申请日：1990-12-07

Applicant: TOKUYAMA SODA KK

Inventor： ISHIZAKI MASAHIKO ,  KITAJIMA TOSHIO

IPC: B01J31/02 ,  C07B61/00 ,  C07D333/32 ,  C07D333/38 ,  C07D333/42

Abstract: PURPOSE:To obtain the subject derivative useful as agricultural chemicals, medicines, etc., in excellent selectivity and high yield by reacting a 3- hydroxythiophenecarboxylic acid derivative with a sulfonic acid derivative in the presence of a specific ammonium salt catalyst in a halogen-based solvent- water system. CONSTITUTION:A 3-hydroxythiophenecarboxylic acid derivative expressed by formula I [A is alkali metal; R1 is cyano, alkoxycarbonyl, phenoxycarbonyl or aminocarbonyl ; R2 is H, halogen, (substituted) alkyl, (substituted) phenyl, etc.] is reacted with a sulfonic acid derivative expressed by formula II (R3 is alkyl; R4 is alkyl, phenyl or tosyl) in the presence of an ammonium salt catalyst expressed by formula III (R5 is iodide ion, bromide ion or hydrogensulfate ion) in a halogen-based solvent-water system to afford the objective 3-alkoxythiophenecarboxylic acid derivative expressed by formula TV.