JPS6160669A - スルホニルグアニジノピリミジン誘導体 - Google Patents

スルホニルグアニジノピリミジン誘導体

Info

Publication number: JPS6160669A
Authority: JP; Japan
Prior art keywords: alkoxy; chlorine; fluorine; alkyl; formula
Prior art date: 1984-08-30
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.): Pending

Application number

JP18871085A

Other languages

English (en)

Japanese (ja)

Inventor

ハンス‐ヨアヒム・デイール

クリスタ・フエスト

ロルフ・キルステン

ヨアヒム・クルト

クラウス‐ヘルムート・ミユラー

テオドール・プフイスター

ウベ・プリースニツツ

ハンス‐ヨツヘム・リーベル

ボルフガング・ロイ

ハンス‐ヨアヒム・ザンテル

ロベルト・アール・シユミツト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1984-08-30

Filing date

1985-08-29

Publication date

1986-03-28

1985-08-29 Application filed by Bayer AG filed Critical Bayer AG

1986-03-28 Publication of JPS6160669A publication Critical patent/JPS6160669A/ja

Status Pending legal-status Critical Current

Links

RICXFEVJGAUCQQ-UHFFFAOYSA-N 2-pyrimidin-2-yl-1-sulfonylguanidine Chemical class S(=O)(=O)=NC(NC1=NC=CC=N1)=N RICXFEVJGAUCQQ-UHFFFAOYSA-N 0.000 title claims description 22
239000000460 chlorine Substances 0.000 claims description 160
229910052801 chlorine Inorganic materials 0.000 claims description 159
239000011737 fluorine Substances 0.000 claims description 151
229910052731 fluorine Inorganic materials 0.000 claims description 151
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 149
-1 benzyloxy-aminosulfonyl Chemical group 0.000 claims description 109
125000001153 fluoro group Chemical group F* 0.000 claims description 99
238000000034 method Methods 0.000 claims description 96
150000001875 compounds Chemical class 0.000 claims description 91
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 89
229910052794 bromium Inorganic materials 0.000 claims description 89
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 88
229910052739 hydrogen Inorganic materials 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 85
125000004093 cyano group Chemical group *C#N 0.000 claims description 74
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
239000002253 acid Substances 0.000 claims description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 42
239000003085 diluting agent Substances 0.000 claims description 41
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 31
239000000126 substance Substances 0.000 claims description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 21
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 18
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
FRQBQBUHPNYTGS-UHFFFAOYSA-N 2-pyrimidin-2-ylguanidine Chemical class NC(N)=NC1=NC=CC=N1 FRQBQBUHPNYTGS-UHFFFAOYSA-N 0.000 claims description 10
DRYYOLGDWVJUCL-UHFFFAOYSA-N pyrimidin-2-ylcyanamide Chemical class N#CNC1=NC=CC=N1 DRYYOLGDWVJUCL-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
239000004009 herbicide Substances 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
ICWOWDKXFBCCMZ-UHFFFAOYSA-N (6-sulfonyl-1H-pyrimidin-2-yl)thiourea Chemical class S(=O)(=O)=C1NC(=NC=C1)NC(S)=N ICWOWDKXFBCCMZ-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
150000005005 aminopyrimidines Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
230000002363 herbicidal effect Effects 0.000 claims description 4
150000002736 metal compounds Chemical class 0.000 claims description 4
229910000000 metal hydroxide Inorganic materials 0.000 claims description 4
150000004692 metal hydroxides Chemical class 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
150000004678 hydrides Chemical class 0.000 claims description 3
239000003701 inert diluent Substances 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
150000002902 organometallic compounds Chemical class 0.000 claims description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
LMRQCRYZDFKPIC-UHFFFAOYSA-N carbamothioyl isocyanate Chemical compound NC(=S)N=C=O LMRQCRYZDFKPIC-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
239000000706 filtrate Substances 0.000 claims description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
230000008635 plant growth Effects 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
125000006323 alkenyl amino group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
239000007858 starting material Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 23
239000000243 solution Substances 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
241000196324 Embryophyta Species 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 20
238000002360 preparation method Methods 0.000 description 20
238000000967 suction filtration Methods 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
239000000370 acceptor Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
239000011230 binding agent Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000000843 powder Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
244000062793 Sorghum vulgare Species 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000012973 diazabicyclooctane Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
239000011591 potassium Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
241000209117 Panicum Species 0.000 description 4
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000004020 conductor Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical group 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
235000011684 Sorghum saccharatum Nutrition 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
238000007792 addition Methods 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
244000309464 bull Species 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000001276 controlling effect Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002357 guanidines Chemical class 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229910052740 iodine Chemical group 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
HUNUAFNLLYVTQD-UHFFFAOYSA-N methyl 2-chlorosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(Cl)(=O)=O HUNUAFNLLYVTQD-UHFFFAOYSA-N 0.000 description 3
235000013336 milk Nutrition 0.000 description 3
239000008267 milk Substances 0.000 description 3
210000004080 milk Anatomy 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
GJWHFBXGZZFPPH-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfonylguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=CC=C1Cl GJWHFBXGZZFPPH-UHFFFAOYSA-N 0.000 description 2
KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
244000099147 Ananas comosus Species 0.000 description 2
241001666377 Apera Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
239000004604 Blowing Agent Substances 0.000 description 2
241000209200 Bromus Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
235000000509 Chenopodium ambrosioides Nutrition 0.000 description 2
244000098897 Chenopodium botrys Species 0.000 description 2
235000005490 Chenopodium botrys Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000219122 Cucurbita Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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235000005822 corn Nutrition 0.000 description 1
JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
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239000002837 defoliant Substances 0.000 description 1
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125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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235000013399 edible fruits Nutrition 0.000 description 1
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229960003750 ethyl chloride Drugs 0.000 description 1
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238000000605 extraction Methods 0.000 description 1
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239000007789 gas Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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150000004679 hydroxides Chemical class 0.000 description 1
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239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
201000007647 intestinal volvulus Diseases 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
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239000000787 lecithin Substances 0.000 description 1
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229920005610 lignin Polymers 0.000 description 1
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235000020640 mackerel Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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235000009973 maize Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
DZNIVKJHYLMSST-UHFFFAOYSA-N methyl 2-(chlorosulfonylmethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CS(Cl)(=O)=O DZNIVKJHYLMSST-UHFFFAOYSA-N 0.000 description 1
VWRBTCLQNSINFV-UHFFFAOYSA-N methyl 4-[(diaminomethylideneamino)oxymethyl]benzoate Chemical compound COC(=O)C1=CC=C(CON=C(N)N)C=C1 VWRBTCLQNSINFV-UHFFFAOYSA-N 0.000 description 1
125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
108091055813 miR-6 stem-loop Proteins 0.000 description 1
108091065445 miR-6-4 stem-loop Proteins 0.000 description 1
108091053743 miR-6-5 stem-loop Proteins 0.000 description 1
108091055911 miR-6-6 stem-loop Proteins 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
BZCGWAXQDLXLQM-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O.ClP(Cl)(Cl)=O BZCGWAXQDLXLQM-UHFFFAOYSA-N 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
MCCLFFQZNBEOAV-UHFFFAOYSA-N pyrimidin-2-ylthiourea Chemical compound NC(=S)NC1=NC=CC=N1 MCCLFFQZNBEOAV-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000010453 quartz Substances 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
238000009367 silviculture Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
SPCSAIAKCMKSJN-UHFFFAOYSA-M sodium;2-chlorobenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1Cl SPCSAIAKCMKSJN-UHFFFAOYSA-M 0.000 description 1
239000002364 soil amendment Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP18871085A 1984-08-30 1985-08-29 スルホニルグアニジノピリミジン誘導体 Pending JPS6160669A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3431924.7		1984-08-30
DE3431924		1984-08-30
DE3517842.6		1985-05-17

Publications (1)

Publication Number	Publication Date
JPS6160669A true JPS6160669A (ja)	1986-03-28

Family

ID=6244296

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP18871085A Pending JPS6160669A (ja)	1984-08-30	1985-08-29	スルホニルグアニジノピリミジン誘導体

Country Status (3)

Country	Link
JP (1)	JPS6160669A (de)
DD (1)	DD238190A5 (de)
ZA (1)	ZA856589B (de)

1985
- 1985-08-28 DD DD28007585A patent/DD238190A5/de unknown
- 1985-08-29 ZA ZA856589A patent/ZA856589B/xx unknown
- 1985-08-29 JP JP18871085A patent/JPS6160669A/ja active Pending

Also Published As

Publication number	Publication date
DD238190A5 (de)	1986-08-13
ZA856589B (en)	1986-04-30

Publication	Publication Date	Title
CA1233180A (en)	1988-02-23	Guanidine derivatives
US4214890A (en)	1980-07-29	Herbicidal pyrimidine and triazine sulfonamides
US4881965A (en)	1989-11-21	Wheat growing process utilizing selective herebicide
CA1231098A (en)	1988-01-05	Pyrimidine derivatives having a herbicidal action and an action regulating plant growth, and the production and use thereof
BG61517B2 (bg)	1997-10-31	N-фенилсулфонил-n'-триазинилкарбамиди
JPH0393783A (ja)	1991-04-18	置換スルホニルアミノアゾール類
JP2572954B2 (ja)	1997-01-16	除草性ピリジンスルフオニルウレア類
JPH0267262A (ja)	1990-03-07	硫黄を経て結合した置換基をもつ（ヘテロ）アリールオキシナフタレン
EP0224842B1 (de)	1992-02-05	Pyrazolsulfonamide-Derivate, Verfahren zu deren Herstellung und diese enthaltende herbizide Mittel
JPS6075468A (ja)	1985-04-27	Ｎ−アリ−ルスルホニル−ｎ′−（４−メルカプトメチル−ピリミジニル−およびトリアジニル）−尿素誘導体、その製造法、並びに除草および植物生長調節用組成物
EP0173958A2 (de)	1986-03-12	1-(2-Oxyaminocarbonylphenylsulfonyl)-3-heteroaryl-harnstoffe
CA1221699A (en)	1987-05-12	N'-(4,5,6-trisubstituted-pyrimidin-2-yl)-n''(di) substituted-n''-(di)substituted-n'''-(substituted- benzenesulphonyl)-guanidines
JPS6160669A (ja)	1986-03-28	スルホニルグアニジノピリミジン誘導体
EP0173322B1 (de)	1988-12-28	(1-(2-Oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe
EP0224078A1 (de)	1987-06-03	Thienylsulfonylguanidin-Derivate
JPH0566955B2 (de)	1993-09-22
CA1218366A (en)	1987-02-24	Herbicidally active n.sup.1,n.sup.2- disubstituted-n-azolecarboxamidines
JPH0225467A (ja)	1990-01-26	アミノグアニジノアジン、その製造方法及び除草剤
US4761173A (en)	1988-08-02	Herbicidal heterocyclic sulfonamides
JPS63150279A (ja)	1988-06-22	除草及び植物生長調節特性を有する新規な化合物、それらの製造方法、並びに該化合物を含有する組成物
JPS62190170A (ja)	1987-08-20	アシル化スルホニルグアニジン類
DD246246A5 (de)	1987-06-03	Herbizide mittel
CA1227205A (en)	1987-09-22	Sulphonylisothioureidopyrimidine derivative
DE3517821A1 (de)	1986-03-13	Sulfonylguanidinotriazin-derivate
DD264840A5 (de)	1989-02-15	Herbizide und pflanzenwuchsregulierende mittel