CA1128047A - Pyridine-sulfonamides pour l'agriculture - Google Patents

Pyridine-sulfonamides pour l'agriculture

Info

Publication number: CA1128047A
Authority: CA; Canada
Prior art keywords: och3; compounds; loc; oca3; solvent
Prior art date: 1978-12-04
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

Application number

CA382,435A

Other languages

English (en)

Inventor

George Levitt

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1978-12-04

Filing date

1981-07-23

Publication date

1982-07-20

1979-12-03 Priority claimed from CA341,112A external-priority patent/CA1114819A/fr

1981-07-23 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1981-07-23 Priority to CA382,435A priority Critical patent/CA1128047A/fr

1982-07-20 Application granted granted Critical

1982-07-20 Publication of CA1128047A publication Critical patent/CA1128047A/fr

Status Expired legal-status Critical Current

Links

DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 title abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 64
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 abstract description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 4
230000002363 herbicidal effect Effects 0.000 abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 456
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 137
239000000460 chlorine Substances 0.000 description 40
239000002904 solvent Substances 0.000 description 36
-1 thienyl radical Chemical class 0.000 description 36
239000000203 mixture Substances 0.000 description 29
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 22
240000008042 Zea mays Species 0.000 description 22
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 22
235000002017 Zea mays subsp mays Nutrition 0.000 description 22
235000005822 corn Nutrition 0.000 description 22
238000000034 method Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
241000209140 Triticum Species 0.000 description 21
235000021307 Triticum Nutrition 0.000 description 21
239000007787 solid Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
150000003839 salts Chemical class 0.000 description 20
244000075850 Avena orientalis Species 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
235000010469 Glycine max Nutrition 0.000 description 17
241000196324 Embryophyta Species 0.000 description 16
244000068988 Glycine max Species 0.000 description 16
240000007594 Oryza sativa Species 0.000 description 16
235000007164 Oryza sativa Nutrition 0.000 description 16
235000009566 rice Nutrition 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
241000209072 Sorghum Species 0.000 description 14
235000011684 Sorghum saccharatum Nutrition 0.000 description 14
235000007320 Avena fatua Nutrition 0.000 description 13
241000192043 Echinochloa Species 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000000725 suspension Substances 0.000 description 13
244000075634 Cyperus rotundus Species 0.000 description 12
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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
239000004615 ingredient Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
235000005373 Uvularia sessilifolia Nutrition 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000008187 granular material Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
244000037364 Cinnamomum aromaticum Species 0.000 description 10
235000014489 Cinnamomum aromaticum Nutrition 0.000 description 10
244000152970 Digitaria sanguinalis Species 0.000 description 10
235000010823 Digitaria sanguinalis Nutrition 0.000 description 10
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
235000005853 Cyperus esculentus Nutrition 0.000 description 9
235000001602 Digitaria X umfolozi Nutrition 0.000 description 9
235000017898 Digitaria ciliaris Nutrition 0.000 description 9
235000005476 Digitaria cruciata Nutrition 0.000 description 9
235000006830 Digitaria didactyla Nutrition 0.000 description 9
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 9
235000014716 Eleusine indica Nutrition 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
240000001549 Ipomoea eriocarpa Species 0.000 description 8
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 8
241001506766 Xanthium Species 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000004009 herbicide Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
235000007319 Avena orientalis Nutrition 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
150000002540 isothiocyanates Chemical class 0.000 description 7
239000008188 pellet Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
229940124530 sulfonamide Drugs 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
239000004563 wettable powder Substances 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
150000005005 aminopyrimidines Chemical class 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
229940101209 mercuric oxide Drugs 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000002245 particle Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
239000008096 xylene Substances 0.000 description 5
240000006995 Abutilon theophrasti Species 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
240000008067 Cucumis sativus Species 0.000 description 4
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
235000004431 Linum usitatissimum Nutrition 0.000 description 4
240000006240 Linum usitatissimum Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
241001355178 Setaria faberi Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229940074993 carbon disulfide Drugs 0.000 description 4
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229940093499 ethyl acetate Drugs 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
235000011167 hydrochloric acid Nutrition 0.000 description 4
229960000443 hydrochloric acid Drugs 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
231100001184 nonphytotoxic Toxicity 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 4
238000001665 trituration Methods 0.000 description 4
235000009854 Cucurbita moschata Nutrition 0.000 description 3
240000001980 Cucurbita pepo Species 0.000 description 3
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235000017016 Setaria faberi Nutrition 0.000 description 3
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230000002218 hypoglycaemic effect Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
JRMWPPYAXFAARO-UHFFFAOYSA-N n-(sulfanylidenemethylidene)pyridine-2-sulfonamide Chemical class S=C=NS(=O)(=O)C1=CC=CC=N1 JRMWPPYAXFAARO-UHFFFAOYSA-N 0.000 description 3
229910052625 palygorskite Inorganic materials 0.000 description 3
238000003359 percent control normalization Methods 0.000 description 3
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FMLHTZVGNSACKP-UHFFFAOYSA-N pyridin-2-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=N1 FMLHTZVGNSACKP-UHFFFAOYSA-N 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
235000020354 squash Nutrition 0.000 description 3
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CJBVRHGBQSEGKP-UHFFFAOYSA-N 1-pyridin-2-ylsulfonyl-3-(triazin-4-yl)urea Chemical class C=1C=CC=NC=1S(=O)(=O)NC(=O)NC1=CC=NN=N1 CJBVRHGBQSEGKP-UHFFFAOYSA-N 0.000 description 2
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
YCGALNBVCTXRTL-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)pyridine-3-sulfonamide Chemical compound ClC1=NC=CC=C1S(=O)(=O)N=C=O YCGALNBVCTXRTL-UHFFFAOYSA-N 0.000 description 2
ROGCSHJTABNAIZ-UHFFFAOYSA-N 2-sulfamoylpyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1S(N)(=O)=O ROGCSHJTABNAIZ-UHFFFAOYSA-N 0.000 description 2
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 2
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KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
244000056139 Brassica cretica Species 0.000 description 2
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QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
101100506034 Fibrobacter succinogenes (strain ATCC 19169 / S85) cel-3 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
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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235000010216 calcium carbonate Nutrition 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
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VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
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239000005457 ice water Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
235000010460 mustard Nutrition 0.000 description 2
DODXZJLHTDSXCR-UHFFFAOYSA-N n-(oxomethylidene)pyridine-2-sulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=N1 DODXZJLHTDSXCR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
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150000007524 organic acids Chemical class 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
ITDILCKJWZMLNW-UHFFFAOYSA-N pyridin-2-ylsulfonylthiourea Chemical class NC(=S)NS(=O)(=O)C1=CC=CC=N1 ITDILCKJWZMLNW-UHFFFAOYSA-N 0.000 description 2
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239000008247 solid mixture Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
GRDFJUXFGKOFCS-UHFFFAOYSA-N sulfanylidenemethanesulfonohydrazide Chemical class NNS(=O)(=O)C=S GRDFJUXFGKOFCS-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229910002029 synthetic silica gel Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)

CA382,435A 1978-12-04 1981-07-23 Pyridine-sulfonamides pour l'agriculture Expired CA1128047A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA382,435A CA1128047A (fr)	1978-12-04	1981-07-23	Pyridine-sulfonamides pour l'agriculture

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US96625878A	1978-12-04	1978-12-04
US966,258		1978-12-04
US8375379A	1979-10-22	1979-10-22
US083,753		1979-10-22
CA341,112A CA1114819A (fr)	1978-12-04	1979-12-03	Sulfonamides de pyridine utilises en agriculture
CA382,435A CA1128047A (fr)	1978-12-04	1981-07-23	Pyridine-sulfonamides pour l'agriculture

Publications (1)

Publication Number	Publication Date
CA1128047A true CA1128047A (fr)	1982-07-20

Family

ID=27426203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA382,435A Expired CA1128047A (fr)	1978-12-04	1981-07-23	Pyridine-sulfonamides pour l'agriculture

Country Status (1)

Country	Link
CA (1)	CA1128047A (fr)

1981
- 1981-07-23 CA CA382,435A patent/CA1128047A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-07-20	MKEX	Expiry

Publication	Publication Date	Title
CA1114819A (fr)	1981-12-22	Sulfonamides de pyridine utilises en agriculture
US4435206A (en)	1984-03-06	Agricultural pyridinesulfonamides
US4544401A (en)	1985-10-01	Agricultural pyridinesulfonamides
EP0007687B1 (fr)	1983-03-30	Sulfonamides, procédés pour leur préparation, compositions contenant ces sulfonamides et un procédé pour la régulation de la croissance des plantes
EP0004163B1 (fr)	1982-06-09	Sulfamates herbicides, leur préparation et leur utilisation
CA1100133A (fr)	1981-04-28	Sulfonamide herbicide
CA1143732A (fr)	1983-03-29	Sulfonamides herbicides
US4214890A (en)	1980-07-29	Herbicidal pyrimidine and triazine sulfonamides
CA1159066A (fr)	1983-12-20	Sulfonamides herbicides
EP0009419B1 (fr)	1986-01-02	Sulfonamides pour l'agriculture, leur préparation et leur utilisation
IE52742B1 (en)	1988-02-03	Thiophene herbicides
US4302241A (en)	1981-11-24	Agricultural sulfonamides
US4348219A (en)	1982-09-07	Herbicidal sulfonamides
CA1204113A (fr)	1986-05-06	Sulfonamides herbicides
EP0048143A1 (fr)	1982-03-24	Sulfonamides herbicides
IE47218B1 (en)	1984-01-25	Herbicidal sulfonamides
US4221585A (en)	1980-09-09	N-[(2,6-Dimethoxypyrimidin-4-yl)]aminocarbonyl benzene sulfonamides and their herbicidal compositions and methods of use
CA1157021A (fr)	1983-11-15	Urees et iso-urees pour l'agriculture
US4231784A (en)	1980-11-04	Herbicidal sulfonamides
US4522645A (en)	1985-06-11	Agricultural pyridinesulfonamides
CA1203533A (fr)	1986-04-22	Sulfonamides herbicides
EP0039239B1 (fr)	1986-02-26	Pyrrole-sulfonamides à activité herbicide
CA1144923A (fr)	1983-04-19	Sulfonamides herbicides
CA1198108A (fr)	1985-12-17	Sylfamates herbicides
EP0001485B1 (fr)	1982-05-12	Sulfonamides herbicides, leur préparation, compositions les contenant et leur utilisation