JPS645593B2 - - Google Patents
Info
- Publication number
- JPS645593B2 JPS645593B2 JP16098581A JP16098581A JPS645593B2 JP S645593 B2 JPS645593 B2 JP S645593B2 JP 16098581 A JP16098581 A JP 16098581A JP 16098581 A JP16098581 A JP 16098581A JP S645593 B2 JPS645593 B2 JP S645593B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- mixture
- formula
- ethylene chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
- 239000007795 chemical reaction product Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- FUQHJLWTRNTWRC-UHFFFAOYSA-N (2,5-dioxopyrrol-3-yl)urea Chemical class NC(=O)NC1=CC(=O)NC1=O FUQHJLWTRNTWRC-UHFFFAOYSA-N 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 58
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 44
- 239000013078 crystal Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000001816 cooling Methods 0.000 description 23
- 239000012044 organic layer Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 241000209094 Oryza Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 235000009566 rice Nutrition 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 13
- TUZVMPXGFZSNBG-UHFFFAOYSA-N 3-aminopyrrole-2,5-dione Chemical compound NC1=CC(=O)NC1=O TUZVMPXGFZSNBG-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000011081 inoculation Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- -1 3 -amino-4-ethoxycarbonyl-1-chlorophenylmaleimide Chemical compound 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- PPSSZWOYSHYRJP-UHFFFAOYSA-N 1,3-bis[(4-methoxyphenyl)methyl]urea Chemical compound C1=CC(OC)=CC=C1CNC(=O)NCC1=CC=C(OC)C=C1 PPSSZWOYSHYRJP-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- ZNQCSLYENQIUMJ-UHFFFAOYSA-N 4,4'-dichlorocarbanilide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 ZNQCSLYENQIUMJ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001329967 Oryzeae Species 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SCYOJLAMDVBOAE-UHFFFAOYSA-N ethyl 2,5-dioxopyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CC(=O)NC1=O SCYOJLAMDVBOAE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16098581A JPS5865273A (ja) | 1981-10-12 | 1981-10-12 | カルバモイルアミノマレイミド類およびその製法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16098581A JPS5865273A (ja) | 1981-10-12 | 1981-10-12 | カルバモイルアミノマレイミド類およびその製法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5865273A JPS5865273A (ja) | 1983-04-18 |
JPS645593B2 true JPS645593B2 (de) | 1989-01-31 |
Family
ID=15726370
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16098581A Granted JPS5865273A (ja) | 1981-10-12 | 1981-10-12 | カルバモイルアミノマレイミド類およびその製法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5865273A (de) |
-
1981
- 1981-10-12 JP JP16098581A patent/JPS5865273A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5865273A (ja) | 1983-04-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU683383B2 (en) | Amino acid amide derivative, process for producing the same,agrohorticultural fungicide, and fungicidal method | |
US4220655A (en) | Pesticidal 5-oxo-2,5 dihydropyrrole | |
US4957919A (en) | 1-aminomethyl-3-aryl-4-cyano-pyrroles and use as fungicides | |
HU208225B (en) | Fungicidal compositions comprising amino acid amide derivatives as active ingredient and process for producing the active ingredients | |
DE69132451T2 (de) | Heterocyclisch substituiertes benzolderivat, dessen darstellung und herbizid, welches dieses als wirkstoff enthält | |
JPS5953917B2 (ja) | テトラヒドロイソフタルイミド誘導体およびその製造方法 | |
Okawara et al. | Convenient syntheses of cyclic carboxamides from α, β, γ, δ and ε-halocarboxamides under phase transfer conditions | |
JPS5865297A (ja) | 複素環式フエニルエ−テル、それらの製造方法およびそれらを含有する除草剤ならびに生長調整剤 | |
JPS645593B2 (de) | ||
CA1157874A (en) | Hydantoin derivatives and process for preparing the same | |
EP0635485B1 (de) | Tetrahydrophthalimid derivate, zwischenprodukte zu deren herstellung, verfahren zur herstellung beider sowie diese als wirksame bestandteile enthaltende herbizide | |
AU609973B2 (en) | 3-cyano-4-phenyl-pyrrole derivatives | |
US4935053A (en) | Unsaturated haloacetanilides | |
WO1995010509A1 (fr) | Derive de 4-imino-oxazolidin-2-one, procede pour produire ce compose et herbicide contenant ce compose comme principe actif | |
US4724261A (en) | Cyclic ureas | |
JPH0625127A (ja) | テトラヒドロフタラミド誘導体、その製造方法及びそれらを有効成分とする除草剤 | |
US4977182A (en) | Fungicidal 3-cyano-4-phenyl-pyrroles | |
JPS61267569A (ja) | 4−オキソ−4h−ピラン−3−カルボキサミド化合物の製造法 | |
US4966968A (en) | Indan derivatives | |
US4010174A (en) | Thiazolinone-(2)-carboxylic acid esters and process therefor | |
EP0244810A1 (de) | Verfahren zur Herstellung von 2-Oxazolidinonen | |
JPS5862154A (ja) | N−スルホニルアミジンカルボン酸アミド類およびその製法 | |
Mao et al. | Synthesis and insecticidal evaluation of novel N‐oxalyl derivatives of diacylhydrazines containing methylcarbamate moieties | |
Wang et al. | Synthesis and biological activity of novel N‐benzoyl‐N‐tert‐butyl‐N′‐(β‐triphenylgermyl) propionylhydrazines | |
JPH10182616A (ja) | アミノ酸アミド誘導体及び農園芸用殺菌剤 |