CA1340326C - Derives de pyrazolesulfonylurees; preparation; herbicide a base du derive comme ingredient actif; methode utilisant cet herbicide - Google Patents

Derives de pyrazolesulfonylurees; preparation; herbicide a base du derive comme ingredient actif; methode utilisant cet herbicide

Info

Publication number: CA1340326C
Authority: CA; Canada
Prior art keywords: groups; group; och3; alkyl; hydrogen atom
Prior art date: 1982-02-27
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 - Lifetime

Application number

CA 422309

Other languages

English (en)

Inventor

Fumio Suzuki

Yoshihiro Iwasawa

Toshiaki Sato

Takasi Ikai

Tosihiko Oguti

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.)

Nissan Chemical Corp

Original Assignee

Nissan Chemical Corp

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.)

1982-02-27

Filing date

1983-02-24

Publication date

1999-01-19

1982-02-27 Priority claimed from JP3137782A external-priority patent/JPS58148879A/ja

1982-08-18 Priority claimed from JP14206982A external-priority patent/JPS5931775A/ja

1982-12-28 Priority claimed from JP22826182A external-priority patent/JPS59122488A/ja

1983-02-24 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1999-01-19 Application granted granted Critical

1999-01-19 Publication of CA1340326C publication Critical patent/CA1340326C/fr

2016-01-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 28
230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
239000004009 herbicide Substances 0.000 title abstract description 17
239000004480 active ingredient Substances 0.000 title abstract description 14
238000002360 preparation method Methods 0.000 title abstract description 6
VMFDZAIIYSKZDE-UHFFFAOYSA-N 1h-pyrazol-5-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C=1C=CNN=1 VMFDZAIIYSKZDE-UHFFFAOYSA-N 0.000 title abstract description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 311
150000001875 compounds Chemical class 0.000 claims description 122
239000000203 mixture Substances 0.000 claims description 73
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 26
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
-1 methoxy, ethoxy, n-propoxy Chemical group 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
JODLVPICEBXFLC-UHFFFAOYSA-N methyl 4-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]-2,5-dimethylpyrazole-3-carboxylate Chemical compound CC1=NN(C)C(C(=O)OC)=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 JODLVPICEBXFLC-UHFFFAOYSA-N 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical compound C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 62
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
229910052731 fluorine Inorganic materials 0.000 claims 5
125000004438 haloalkoxy group Chemical group 0.000 claims 4
230000002194 synthesizing effect Effects 0.000 claims 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
DOOBDQKWSOUEQB-UHFFFAOYSA-N methyl 4-[(4-chloro-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]-2,5-dimethylpyrazole-3-carboxylate Chemical compound CC1=NN(C)C(C(=O)OC)=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(Cl)=N1 DOOBDQKWSOUEQB-UHFFFAOYSA-N 0.000 claims 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1532
230000015572 biosynthetic process Effects 0.000 description 54
238000003786 synthesis reaction Methods 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000013078 crystal Substances 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
229940124530 sulfonamide Drugs 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
YCJLAFPDKVXMOO-UHFFFAOYSA-N 4-n,4-n,2,5-tetramethylpyrazole-3,4-disulfonamide Chemical compound CN(C)S(=O)(=O)C=1C(C)=NN(C)C=1S(N)(=O)=O YCJLAFPDKVXMOO-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000004563 wettable powder Substances 0.000 description 18
238000009472 formulation Methods 0.000 description 17
239000005457 ice water Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000002904 solvent Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 11
LSJVQKDTVCDSPE-UHFFFAOYSA-N 1h-pyrazole-5-sulfonamide Chemical class NS(=O)(=O)C=1C=CNN=1 LSJVQKDTVCDSPE-UHFFFAOYSA-N 0.000 description 11
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
241000196324 Embryophyta Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
239000003945 anionic surfactant Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 9
229960000443 hydrochloric acid Drugs 0.000 description 9
235000011167 hydrochloric acid Nutrition 0.000 description 9
239000002736 nonionic surfactant Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
150000003456 sulfonamides Chemical class 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
240000007594 Oryza sativa Species 0.000 description 8
239000004927 clay Substances 0.000 description 8
238000001035 drying Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000005995 Aluminium silicate Substances 0.000 description 7
235000007164 Oryza sativa Nutrition 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
235000012211 aluminium silicate Nutrition 0.000 description 7
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
KSEMETYAQIUBQB-UHFFFAOYSA-N n,n-diethylmethanesulfonamide Chemical compound CCN(CC)S(C)(=O)=O KSEMETYAQIUBQB-UHFFFAOYSA-N 0.000 description 6
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 5
239000000440 bentonite Substances 0.000 description 5
229910000278 bentonite Inorganic materials 0.000 description 5
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
238000005507 spraying Methods 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
SNWZXTZIZWBIDQ-UHFFFAOYSA-N 4-methoxy-6-methylpyrimidin-2-amine Chemical compound COC1=CC(C)=NC(N)=N1 SNWZXTZIZWBIDQ-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
244000058871 Echinochloa crus-galli Species 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000013256 coordination polymer Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
UOKDEVVNDSYMRY-UHFFFAOYSA-N ethyl 5-chloro-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1Cl UOKDEVVNDSYMRY-UHFFFAOYSA-N 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
MPKIDHIOYNMFES-CLTBVUQJSA-N 1-O-(alpha-D-galactopyranosyl)-N-tetracosanyl-2-aminononane-1,3,4-triol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O MPKIDHIOYNMFES-CLTBVUQJSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
DDUSLFAWARYAPR-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole Chemical compound CC=1C=C(Cl)N(C)N=1 DDUSLFAWARYAPR-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
ICDLJCWXRUNUNO-UHFFFAOYSA-N ethyl 1-methyl-5-sulfamoylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1S(N)(=O)=O ICDLJCWXRUNUNO-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
IJBWWMGSVFDSRP-UHFFFAOYSA-N n-(oxomethylidene)-1h-pyrazole-5-sulfonamide Chemical class O=C=NS(=O)(=O)C=1C=CNN=1 IJBWWMGSVFDSRP-UHFFFAOYSA-N 0.000 description 3
239000011369 resultant mixture Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000005406 washing Methods 0.000 description 3
CLZVIULAQUSRCK-UHFFFAOYSA-N 1,3-dimethyl-5-propylsulfonylpyrazole-4-sulfonamide Chemical compound CCCS(=O)(=O)C1=C(S(N)(=O)=O)C(C)=NN1C CLZVIULAQUSRCK-UHFFFAOYSA-N 0.000 description 2
IGSVDLHSCMWCNW-UHFFFAOYSA-N 1,5-dimethyl-3-(trifluoromethyl)pyrazole-4-sulfonamide Chemical compound CC1=C(S(N)(=O)=O)C(C(F)(F)F)=NN1C IGSVDLHSCMWCNW-UHFFFAOYSA-N 0.000 description 2
MTZYJDHFSVUYQG-UHFFFAOYSA-N 1-butyl-3-(5-methoxy-1,3-dimethylpyrazol-4-yl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C=1C(C)=NN(C)C=1OC MTZYJDHFSVUYQG-UHFFFAOYSA-N 0.000 description 2
IUAIOZJBFUEYQD-UHFFFAOYSA-N 2,5-dimethyl-4-nitropyrazole-3-sulfonamide Chemical compound CC1=NN(C)C(S(N)(=O)=O)=C1[N+]([O-])=O IUAIOZJBFUEYQD-UHFFFAOYSA-N 0.000 description 2
YJTCAXYRVVGBEL-UHFFFAOYSA-N 2,5-dimethylpyrazole-3-sulfonamide Chemical compound CC=1C=C(S(N)(=O)=O)N(C)N=1 YJTCAXYRVVGBEL-UHFFFAOYSA-N 0.000 description 2
NCQIBCBRKYCKBY-UHFFFAOYSA-N 4-chloro-2,5-dimethylpyrazole-3-sulfonamide Chemical compound CC1=NN(C)C(S(N)(=O)=O)=C1Cl NCQIBCBRKYCKBY-UHFFFAOYSA-N 0.000 description 2
NYDANSQFEDVGJL-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(N)(=O)=O NYDANSQFEDVGJL-UHFFFAOYSA-N 0.000 description 2
SDYOVMHXYNKROV-UHFFFAOYSA-N 5-chloro-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1Cl SDYOVMHXYNKROV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
YRDRWAMQGRODTB-UHFFFAOYSA-N CCOC(=O)C=1C=NN(C)C=1S Chemical compound CCOC(=O)C=1C=NN(C)C=1S YRDRWAMQGRODTB-UHFFFAOYSA-N 0.000 description 2
102100038916 Caspase-5 Human genes 0.000 description 2
240000006122 Chenopodium album Species 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
244000035395 Chenopodium ficifolium Species 0.000 description 2
235000009731 Chenopodium ficifolium Nutrition 0.000 description 2
241000223782 Ciliophora Species 0.000 description 2
240000004230 Cyperus compressus Species 0.000 description 2
241000817048 Cyperus microiria Species 0.000 description 2
240000003176 Digitaria ciliaris Species 0.000 description 2
235000017898 Digitaria ciliaris Nutrition 0.000 description 2
244000152970 Digitaria sanguinalis Species 0.000 description 2
235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
101100506034 Fibrobacter succinogenes (strain ATCC 19169 / S85) cel-3 gene Proteins 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
244000234609 Portulaca oleracea Species 0.000 description 2
235000001855 Portulaca oleracea Nutrition 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000490453 Rorippa Species 0.000 description 2
240000006586 Rorippa indica var. indica Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
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NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
GZWWDXOLGQOTPW-UHFFFAOYSA-N methyl 1,5-dimethyl-4-sulfamoylpyrazole-3-carboxylate Chemical compound COC(=O)C1=NN(C)C(C)=C1S(N)(=O)=O GZWWDXOLGQOTPW-UHFFFAOYSA-N 0.000 description 1
WOBRRDCECRRRGS-UHFFFAOYSA-N methyl 1,5-dimethylpyrazole-3-carboxylate Chemical compound COC(=O)C=1C=C(C)N(C)N=1 WOBRRDCECRRRGS-UHFFFAOYSA-N 0.000 description 1
UNWLBZTZCSGYIE-UHFFFAOYSA-N methyl 1-methyl-5-sulfamoylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C)C=1S(N)(=O)=O UNWLBZTZCSGYIE-UHFFFAOYSA-N 0.000 description 1
GKJMLUXRBGCLOW-UHFFFAOYSA-N methyl 2,5-dimethyl-4-sulfamoylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(S(N)(=O)=O)C(C)=NN1C GKJMLUXRBGCLOW-UHFFFAOYSA-N 0.000 description 1
TULBDXSFRIHALG-UHFFFAOYSA-N methyl 4-(butylcarbamoylsulfamoyl)-2,5-dimethylpyrazole-3-carboxylate Chemical compound CCCCNC(=O)NS(=O)(=O)C=1C(C)=NN(C)C=1C(=O)OC TULBDXSFRIHALG-UHFFFAOYSA-N 0.000 description 1
WWFKXJIODQOSAF-UHFFFAOYSA-N methyl 4-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]-2,5-dimethylpyrazole-3-carboxylate Chemical compound CC1=NN(C)C(C(=O)OC)=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 WWFKXJIODQOSAF-UHFFFAOYSA-N 0.000 description 1
LEDCKSUUGDBFKG-UHFFFAOYSA-N methyl 4-isocyanatosulfonyl-2,5-dimethylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(S(=O)(=O)N=C=O)C(C)=NN1C LEDCKSUUGDBFKG-UHFFFAOYSA-N 0.000 description 1
GDCJVGNBAXFXMI-UHFFFAOYSA-N methyl 5-(butylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Chemical compound CCCCNC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=NN1C GDCJVGNBAXFXMI-UHFFFAOYSA-N 0.000 description 1
GXCHZTZQQJQKAN-UHFFFAOYSA-N methyl 5-chloro-1-methylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C)C=1Cl GXCHZTZQQJQKAN-UHFFFAOYSA-N 0.000 description 1
NCZCSRXAQSKZJN-UHFFFAOYSA-N methyl 5-ethyl-1-methyl-4-sulfamoylpyrazole-3-carboxylate Chemical compound CCC1=C(S(N)(=O)=O)C(C(=O)OC)=NN1C NCZCSRXAQSKZJN-UHFFFAOYSA-N 0.000 description 1
ODDYYVJKFBWQFL-UHFFFAOYSA-N methyl 5-ethyl-1-methylpyrazole-3-carboxylate Chemical compound CCC1=CC(C(=O)OC)=NN1C ODDYYVJKFBWQFL-UHFFFAOYSA-N 0.000 description 1
HTBABIPYXPNVLZ-UHFFFAOYSA-N methyl 5-ethyl-2-methyl-4-sulfamoylpyrazole-3-carboxylate Chemical compound CCC1=NN(C)C(C(=O)OC)=C1S(N)(=O)=O HTBABIPYXPNVLZ-UHFFFAOYSA-N 0.000 description 1
OATMWWPWCJIWGA-UHFFFAOYSA-N methyl 5-ethyl-2-methylpyrazole-3-carboxylate Chemical compound CCC=1C=C(C(=O)OC)N(C)N=1 OATMWWPWCJIWGA-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ALEBFZNQPWQBOT-UHFFFAOYSA-N n,n,2,5-tetramethyl-4-sulfamoylpyrazole-3-carboxamide Chemical compound CN(C)C(=O)C1=C(S(N)(=O)=O)C(C)=NN1C ALEBFZNQPWQBOT-UHFFFAOYSA-N 0.000 description 1
MVSCTMHOTLKBEV-UHFFFAOYSA-N n,n,2,5-tetramethylpyrazole-3-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NN1C MVSCTMHOTLKBEV-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
SZPIUVZVSIKQDF-UHFFFAOYSA-N prop-1-enyl 4-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]-2,5-dimethylpyrazole-3-carboxylate Chemical compound CC1=NN(C)C(C(=O)OC=CC)=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 SZPIUVZVSIKQDF-UHFFFAOYSA-N 0.000 description 1
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
244000082735 tidal marsh flat sedge Species 0.000 description 1
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

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

CA 422309 1982-02-27 1983-02-24 Derives de pyrazolesulfonylurees; preparation; herbicide a base du derive comme ingredient actif; methode utilisant cet herbicide Expired - Lifetime CA1340326C (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP31377/1982		1982-02-27
JP3137782A JPS58148879A (ja)	1982-02-27	1982-02-27	ピラゾ−ルスルホニルウレア誘導体、その製造法および該誘導体を含有する除草剤
JP142069/1982		1982-08-18
JP14206982A JPS5931775A (ja)	1982-08-18	1982-08-18	ピラゾールスルホニルウレア誘導体および除草剤
JP228261/1982		1982-12-28
JP22826182A JPS59122488A (ja)	1982-12-28	1982-12-28	ピラゾ−ルスルホニルウレア誘導体、その製法および該誘導体を含有する除草剤

Publications (1)

Publication Number	Publication Date
CA1340326C true CA1340326C (fr)	1999-01-19

Family

ID=27287302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 422309 Expired - Lifetime CA1340326C (fr)	1982-02-27	1983-02-24	Derives de pyrazolesulfonylurees; preparation; herbicide a base du derive comme ingredient actif; methode utilisant cet herbicide

Country Status (2)

Country	Link
CA (1)	CA1340326C (fr)
MY (1)	MY100991A (fr)

1983
- 1983-02-24 CA CA 422309 patent/CA1340326C/fr not_active Expired - Lifetime
1987
- 1987-12-16 MY MYPI87003208A patent/MY100991A/en unknown

Also Published As

Publication number	Publication date
MY100991A (en)	1991-06-15

Legal Events

Date	Code	Title	Description
2016-03-22	MKEX	Expiry	Effective date: 20160119

Publication	Publication Date	Title
EP0087780B1 (fr)	1991-10-23	Dérivés de pyrazolesulfonylurées, leur préparation, herbicide contenant les dérivés comme substance active et méthode herbicide utilisant l'herbicide
US4689417A (en)	1987-08-25	Pyrazolesulfonylurea amides and chlorides
CA1094067A (fr)	1981-01-20	Sulfonamides a proprietes herbicides
CA1109879A (fr)	1981-09-29	3-aminopyrazoles substituees
BG60335B2 (bg)	1994-07-25	N-фенилсулфонил-n'-триазинил карбамиди
JP2011500745A (ja)	2011-01-06	２−ヨード−ｎ−［（４−メトキシ−６−メチル−１，３，５−トリアジン−２−イル）カルバモイル］ベンゼンスルホンアミドの塩、それらの製造法、並びにそれらの除草剤および植物成長調節剤としての使用
BG61517B2 (bg)	1997-10-31	N-фенилсулфонил-n'-триазинилкарбамиди
JPH03153674A (ja)	1991-07-01	ハロゲン化されたスルホニルアミノカルボニルトリアゾリノン類
NZ208803A (en)	1987-10-30	Heterocyclic sulphonylureas and herbicidal compositions
JPH0211579A (ja)	1990-01-16	スルホニルアミノカルボニルトリアゾリノン類
CA1174681A (fr)	1984-09-18	Triazole urees herbicides
IL90299A (en)	1994-11-28	2-Alkoxifnaoxysol - Phonylureas and preparations for the control of weeds and the regulation of vegetation containing them
NZ243599A (en)	1994-04-27	N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulphonamides and herbicidal compositions
PT96445A (pt)	1991-10-15	Processo para a preparacao de piridil-sulfonil-ureias e de composicoes herbicidas e de regulacao do desenvolvimento de plantas que as contem
HU194190B (en)	1988-01-28	Herbicide compositions containing sulfonyl-urea derivatives as active components and process for producing the active components
US4844728A (en)	1989-07-04	Pyrazolesulfonamide derivative, and herbicide containing it
CA1166249A (fr)	1984-04-24	Indolsulfonamides herbicides
JP2818799B2 (ja)	1998-10-30	複素環式置換基を有するスルホニル尿素、それらの製造方法および除草剤としてのそれらの用途
CA2149239C (fr)	2004-04-13	Sulfonylurees herbicides, preparation et mode d'emploi
US4645527A (en)	1987-02-24	Herbicidal antidotes
CA1244448A (fr)	1988-11-08	5-acylamino-1-phenylpyrazoles substitues
CA1340326C (fr)	1999-01-19	Derives de pyrazolesulfonylurees; preparation; herbicide a base du derive comme ingredient actif; methode utilisant cet herbicide
JPH0421672B2 (fr)	1992-04-13
US4897105A (en)	1990-01-30	Herbicidal compounds, their production and use
JPH02264774A (ja)	1990-10-29	スルホニルイミノ‐アジニルヘテロアゾール、その製造方法、その中間体及びその除草剤としての使用