公开(公告)号：DE69107579T2

公开(公告)日：1995-06-14

申请号：DE69107579

申请日：1991-11-15

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  TSUCHIYA TOURU ,  SHIBUYA ISAO ,  YONEMOTO KATSUMI ,  TAGUCHI YOICHI C O NATIONAL CH

IPC: C07D285/34

Abstract: There is disclosed a method for producing 2,6-bis(disubstituted amino)-4-1,3,5-thiadiazine-4-one compounds represented by formula (I). The method comprises reacting an N,N-disubstituted cyanamide represented by formula (II) with carbonyl sulfide represented by formula (III) under a high pressure. wherein R1 and R2 each represent an alkyl group or R1 and R2 may bond together to form a ring, wherein R1 and R2 each have the same meanings as in formula (I), Formula (III> S = C = O . o

公开(公告)号：DE69107579D1

公开(公告)日：1995-03-30

申请号：DE69107579

申请日：1991-11-15

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  TSUCHIYA TOURU ,  SHIBUYA ISAO ,  YONEMOTO KATSUMI ,  TAGUCHI YOICHI C O NATIONAL CH

IPC: C07D285/34

Abstract: There is disclosed a method for producing 2,6-bis(disubstituted amino)-4-1,3,5-thiadiazine-4-one compounds represented by formula (I). The method comprises reacting an N,N-disubstituted cyanamide represented by formula (II) with carbonyl sulfide represented by formula (III) under a high pressure. wherein R1 and R2 each represent an alkyl group or R1 and R2 may bond together to form a ring, wherein R1 and R2 each have the same meanings as in formula (I), Formula (III> S = C = O . o

公开(公告)号：JPH0527359A

公开(公告)日：1993-02-05

申请号：JP4410991

申请日：1991-02-18

Applicant: AGENCY IND SCIENCE TECHN ,  KONISHIROKU PHOTO IND

Inventor： YONEMOTO KATSUMI ,  SHIBUYA ISAO ,  HIRABAYASHI SHIGETO ,  KANEKO YUTAKA

IPC: G03C1/34

Abstract: PURPOSE:To prevent fogging and to suppress fogging at the time of rapid processing at high temp. by using a specified compd. as an anti-foggant. CONSTITUTION:A compd. represented by formula I is used as an anti-foggant for silver halide photography. In the formula I, each of R1 and R2 is alkyl, R1 and R2 may be different from each other and R3 is alkoxy or dialkylamino. At least one kind of anti-foggant made of the compd. represented by the formula I is incorporated into a silver halide emulsion layer or an adjacent hydrophilic colloidal layer. This anti-foggant inhibits fogging during storage even at high temp. or high temp. and humidity and does not cause the lowering of sensitivity and the softening of gradation.

公开(公告)号：JPH0413658A

公开(公告)日：1992-01-17

申请号：JP11845790

申请日：1990-05-08

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YONEMOTO KATSUMI ,  SHIBUYA ISAO

IPC: C07D295/20 ,  C07C313/28 ,  C07C313/32 ,  C07C313/34 ,  C07C327/28 ,  C07C327/52 ,  C07C333/20 ,  C07D213/81 ,  C07D333/40 ,  C07D405/12 ,  C07D409/12 ,  C07D417/12

Abstract: PURPOSE:To simply and rapidly produce various sulfenamide derivatives in good yield by treating an amide type compound with sodium hydride and then reacting the resultant compound with a disulfide derivative. CONSTITUTION:An amide type compound (e.g. 2-thiophenecarboxyamide) expressed by formula I (R is H, aryl, heterocyclic ring, alkyl, dialkylamino or alkoxy) is treated with sodium hydride and then reacted with a disulfide derivative (e.g. tetraethylthiuram disulfide) expressed by formula II (R is N,N- disubstituted thiocarbamoyl, aroyl, aryl or heterocyclic ring) to afford a sulfenamide derivative [e.g. N-(2-thenoyl)-S-diethylthiocarbamoylsulfenamide] expressed by formula III. Raw materials for the aforementioned method are readily available and reagents are inexpensive. The product has silver halide photographic inhibitory effects on fog.

公开(公告)号：JPS63218682A

公开(公告)日：1988-09-12

申请号：JP5370287

申请日：1987-03-09

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YONEMOTO KATSUMI ,  SHIBUYA ISAO

IPC: C07D327/04 ,  C07D285/00 ,  C07D291/06 ,  C07D339/06 ,  C07D521/00

Abstract: PURPOSE:To simply and inexpensively obtain a ring-expanded product by N atom useful as a synthetic intermediate for agricultural chemicals and medicine under mild conditions in high yield, by reacting a heterocyclic cationic compound with a sulfenamide derivative as a ring expanding reagent. CONSTITUTION:A heterocyclic cationic compound expressed by formula I (X and Y are hetero atoms; R is electron-donating group; Z is acid radical of inorganic strong acid; number of ring member of cation part is 5) such as 5- morpholine-3-phenyl-1,4,2-dithiazolium perchloric acid salt or mesoionic compound expressed by formula II (R is R ; R is inert substituent group; W is S or O) is reacted with a sulfenamide derivative expressed by formula III (R is N,N-disubstituted thiocarbamoylsulfenamide, heterocyclic group, aroyl or substituted imidoyl) such as dimethylthiocarbamoylsulphenamide in a solvent such as acetonitrile under mild conditions of room temperature and neutral for several ten minutes - several days to provide the aimed compound expressed by formula V (numbers of ring member are 6) having antiaromatic properties.

公开(公告)号：JPH04182475A

公开(公告)日：1992-06-30

申请号：JP30925090

申请日：1990-11-15

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  TSUCHIYA TORU ,  TAGUCHI YOICHI ,  SHIBUYA ISAO ,  YONEMOTO KATSUMI

IPC: C07D285/34

Abstract: PURPOSE:To obtain a compound useful as an intermediate for medicine or agricultural chemical in one-stage reaction and good yield from an inexpensive raw material by reacting an N,N-disubstituted-cyanamide with carbonylsulfide under high pressure. CONSTITUTION:A N,N-di-substituted cyanamide expressed by formula I (R1 and R2 are alkyl or R1 and R2 may together form a ring) is reacted with carbonyl sulfide expressed by the formula S=C=O in a solvent such as toluene at 20-200 deg.C under pressure of 1000-12000 atom to provide the objective product expressed by formula II. The compound expressed by formula I and carbonyl sulfide are used at a molar ratio of 1:10 to 10:1. The compound expressed by formula II is used as an intermediate for drug for inflammatory disease and cardiopathy and useful as an intermediate for nematocide, insect pest control agent, etc.

公开(公告)号：JPH0476537A

公开(公告)日：1992-03-11

申请号：JP18943490

申请日：1990-07-19

Applicant: AGENCY IND SCIENCE TECHN ,  KONISHIROKU PHOTO IND

Inventor： SHIBUYA ISAO ,  YONEMOTO KATSUMI ,  HIRABAYASHI SHIGETO ,  KANEKO YUTAKA

IPC: G03C1/34

Abstract: PURPOSE:To maintain stable photographic characteristics in spite of long-time preservation at and under a high temp. and high humidity by incorporating a specific compd. into silver halide emulsion layers and the hydrophilic colloidal layers adjacent thereto. CONSTITUTION:The compd. expressed by formula is used. In the formula, R1 and R2 may be the same or different and respectively denote an alkyl group; R1 and R2 may form a hetero ring by making ring condensation together with a nitrogen atom; R3 denotes a hydrogen atom, halogen atom, alkoxy group, hydroxy group or dialkyl amino group. Then, the fogging is inhibited without generating the degradation in photographic characteristics, such as loss of sensitivity by the generation of the fogging and deterioration of gradation even under severe conditions.

公开(公告)号：JPH03258762A

公开(公告)日：1991-11-19

申请号：JP5578090

申请日：1990-03-07

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIBUYA ISAO ,  YONEMOTO KATSUMI

IPC: C07D333/22 ,  C07C327/26 ,  C07D213/53 ,  C07D521/00

Abstract: NEW MATERIAL:A S-aroylthiooxime of formula I (Ar is aryl which may have a substituent; R is phenyl or heterocyclic group which may have a substituent at the p-position). EXAMPLE:S-Benzoylbenzthiooxime. USE:The compound exhibits a SHG activity and useful as a nonlinear optical material. Since the compound exhibits high reactivity and reacts with various kinds of reagents to give many derivatives, the compound is useful also for synthetic chemistry. PREPARATION:A S-aroylsulfenamide of formula II is reacted with an aldehyde of formula III in the presence of an acid catalyst in an organic solvent at 50-100 deg.C to provide the component of formula I. The compound of formula II is synthesized by dropping a hydroxylamine-O-sulfonic acid aqueous solution into the alkali aqueous solution of an aromatic thiocarboxylic acid at a temperature below room temperature.

公开(公告)号：JPH04364178A

公开(公告)日：1992-12-16

申请号：JP7234591

申请日：1991-03-12

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIBUYA ISAO ,  YONEMOTO KATSUMI ,  TSUCHIYA TORU ,  TAGUCHI YOICHI ,  YASUMOTO MASAHIKO

IPC: B01J27/122 ,  B01J27/25 ,  C07B61/00 ,  C07D327/04

Abstract: PURPOSE:To obtain the subject compound which is synthetic intermediate of sulfur-containing organic compounds such as medicines, agricultural chemicals, etc., without using toxic carbonyl sulfide gas by treating a di-substituted dithiocarbamic acid phenacylethyl with a specific soft metal salt. CONSTITUTION:A compound expressed by formula I (R is di-substituted amino; Ar is phenyl which may have a substituent group) is reacted with a salt of soft metal such as silver, copper (I) or mercury (II) (preferably a silver salt), preferably in an organic solvent such as alcohols in the presence of a strong acid to provide the objective compound expressed by formula II (X is silver radical).

公开(公告)号：JPH01225940A

公开(公告)日：1989-09-08

申请号：JP5307388

申请日：1988-03-07

Applicant: AGENCY IND SCIENCE TECHN ,  KONISHIROKU PHOTO IND ,  SANKYO CO

Inventor： YONEMOTO KATSUMI ,  SHIBUYA ISAO ,  SAKAMOTO HIDEKAZU ,  KANEKO YUTAKA

IPC: G03C1/34

Abstract: PURPOSE:To maintain stable photographic characteristics even after long-term preservation at an under a high temp. and high humidity by forming the fog restrainer of 1,4,2-dithiazolium salt compds. having a specific heteroarom. cation ring structure. CONSTITUTION:This fog restrainer is used by incorporating at least one selected from the 1,4,2-dithiazolium salt compds. having the heteroarom. cation ring structure into at least either of a silver halide emulsion layer and the hydrophilic colloid layer adjacent thereto. The purpose as the fog restrainer for photographs is attained if the 1,4,2-dithiazolium salts have the cation ring structure in this case. Generation of fogging is thereby suppressed during the long-term preservation or even if the photographic sensitive material is stored at a high temp. or at and under the high temp. and high humidity. The excellent photographic sensitive material which is free from degradation of the sensitivity and softening of the gradation is thus obtd.