CA1189073A - Herbicides a base de pyridylsulfone - Google Patents

Herbicides a base de pyridylsulfone

Info

Publication number: CA1189073A
Authority: CA; Canada
Prior art keywords: compound; aminocarbonyl; methylsulfonyl; pyridinesulfonamide; compounds
Prior art date: 1980-03-07
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

CA000372421A

Other languages

English (en)

Inventor

John B. Adams, Jr.

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.)

1980-03-07

Filing date

1981-03-05

Publication date

1985-06-18

1981-03-05 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1985-06-18 Application granted granted Critical

1985-06-18 Publication of CA1189073A publication Critical patent/CA1189073A/fr

Status Expired legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title abstract description 8
USKQCXYRFGJOBQ-UHFFFAOYSA-N 2-pyridin-2-ylsulfonylpyridine Chemical compound C=1C=CC=NC=1S(=O)(=O)C1=CC=CC=N1 USKQCXYRFGJOBQ-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 57
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
238000000034 method Methods 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 2
CUQLLDOMCVEVAZ-UHFFFAOYSA-N 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 CUQLLDOMCVEVAZ-UHFFFAOYSA-N 0.000 claims description 2
YDRGORSCIVZEDQ-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 YDRGORSCIVZEDQ-UHFFFAOYSA-N 0.000 claims description 2
SLNZYGIGCMCEGB-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 SLNZYGIGCMCEGB-UHFFFAOYSA-N 0.000 claims description 2
125000006519 CCH3 Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 6
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
BJZVFIRDAXGOQA-UHFFFAOYSA-N 1-(4,6-dimethyl-1,3,5-triazin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound CC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 BJZVFIRDAXGOQA-UHFFFAOYSA-N 0.000 claims 1
FXMMYBZFROIEKS-UHFFFAOYSA-N 1-(4-methoxy-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound N=1C=2OCCC=2C(OC)=NC=1NC(=O)NS(=O)(=O)C1=CC=CN=C1S(C)(=O)=O FXMMYBZFROIEKS-UHFFFAOYSA-N 0.000 claims 1
VCGMUAIHCWPHJD-UHFFFAOYSA-N 1-(4-methoxy-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound N=1C=2CCCC=2C(OC)=NC=1NC(=O)NS(=O)(=O)C1=CC=CN=C1S(C)(=O)=O VCGMUAIHCWPHJD-UHFFFAOYSA-N 0.000 claims 1
PCBPSLBYKGMPHY-UHFFFAOYSA-N 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 PCBPSLBYKGMPHY-UHFFFAOYSA-N 0.000 claims 1
ZEHJZZDSWHAFGT-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=NC=CC=2)S(C)(=O)=O)=N1 ZEHJZZDSWHAFGT-UHFFFAOYSA-N 0.000 claims 1
NHNYYSNWNSHISY-UHFFFAOYSA-N 1-(4-methyl-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound N=1C=2OCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CN=C1S(C)(=O)=O NHNYYSNWNSHISY-UHFFFAOYSA-N 0.000 claims 1
ZTZHPURBTJDYMU-UHFFFAOYSA-N 1-(4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)-3-(2-methylsulfonylpyridin-3-yl)sulfonylurea Chemical compound N=1C=2CCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CN=C1S(C)(=O)=O ZTZHPURBTJDYMU-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
-1 Pyridyl sulfones Chemical class 0.000 abstract description 29
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 12
230000008635 plant growth Effects 0.000 abstract description 2
230000033228 biological regulation Effects 0.000 abstract 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 55
239000000460 chlorine Substances 0.000 description 31
239000000203 mixture Substances 0.000 description 26
239000007787 solid Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000004615 ingredient Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229940124530 sulfonamide Drugs 0.000 description 9
238000009472 formulation Methods 0.000 description 8
239000008187 granular material Substances 0.000 description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
150000003456 sulfonamides Chemical class 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000008188 pellet Substances 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 5
235000007164 Oryza sativa Nutrition 0.000 description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
150000003457 sulfones Chemical class 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
240000003176 Digitaria ciliaris Species 0.000 description 4
235000017898 Digitaria ciliaris Nutrition 0.000 description 4
235000005476 Digitaria cruciata Nutrition 0.000 description 4
235000006830 Digitaria didactyla Nutrition 0.000 description 4
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
244000058871 Echinochloa crus-galli Species 0.000 description 4
235000014716 Eleusine indica Nutrition 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
235000005822 corn Nutrition 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
150000002500 ions Chemical class 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000005507 spraying Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
240000003829 Sorghum propinquum Species 0.000 description 3
235000011684 Sorghum saccharatum Nutrition 0.000 description 3
241001506766 Xanthium Species 0.000 description 3
229940022682 acetone Drugs 0.000 description 3
239000003472 antidiabetic agent Substances 0.000 description 3
229960000892 attapulgite Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000000227 grinding Methods 0.000 description 3
230000012010 growth Effects 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052625 palygorskite Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-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
USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
244000037364 Cinnamomum aromaticum Species 0.000 description 2
235000014489 Cinnamomum aromaticum Nutrition 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
235000005853 Cyperus esculentus Nutrition 0.000 description 2
244000075634 Cyperus rotundus Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
240000001549 Ipomoea eriocarpa Species 0.000 description 2
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241001300479 Macroptilium Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229940125708 antidiabetic agent Drugs 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
229910052794 bromium Inorganic materials 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
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000006378 damage Effects 0.000 description 2
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000005243 fluidization Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000002218 hypoglycaemic effect Effects 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
FNKUJDADVODZOY-UHFFFAOYSA-N sulfanyl thiohypochlorite Chemical compound SSCl FNKUJDADVODZOY-UHFFFAOYSA-N 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000010998 test method Methods 0.000 description 2
229940035893 uracil Drugs 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
AKDLOHWMYMAHFF-UHFFFAOYSA-N 1-(2,6-dimethoxypyrimidin-4-yl)-3-(4-methylphenyl)sulfonylurea Chemical compound COC1=NC(OC)=CC(NC(=O)NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 AKDLOHWMYMAHFF-UHFFFAOYSA-N 0.000 description 1
IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 1
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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238000005260 corrosion Methods 0.000 description 1
NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
239000003599 detergent Substances 0.000 description 1
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JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
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239000012954 diazonium Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
238000004880 explosion Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000446 fuel Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
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239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000001965 increasing effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
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239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
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 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
BVPSSZAVUQHOML-UHFFFAOYSA-N n-chloropyridin-2-amine Chemical compound ClNC1=CC=CC=N1 BVPSSZAVUQHOML-UHFFFAOYSA-N 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
230000032393 negative regulation of gluconeogenesis Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
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230000002688 persistence Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000012256 powdered iron Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
108010080511 serum sodium transport inhibitor Proteins 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical compound S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 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
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
150000003573 thiols Chemical class 0.000 description 1
PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
238000006692 trifluoromethylation reaction Methods 0.000 description 1
239000013638 trimer Substances 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA000372421A 1980-03-07 1981-03-05 Herbicides a base de pyridylsulfone Expired CA1189073A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US12817680A	1980-03-07	1980-03-07
US128,176		1980-03-07

Publications (1)

Publication Number	Publication Date
CA1189073A true CA1189073A (fr)	1985-06-18

Family

ID=22434023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000372421A Expired CA1189073A (fr)	1980-03-07	1981-03-05	Herbicides a base de pyridylsulfone

Country Status (5)

Country	Link
JP (1)	JPS56139466A (fr)
KR (1)	KR830005165A (fr)
CA (1)	CA1189073A (fr)
PH (1)	PH17301A (fr)
ZA (1)	ZA811484B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4618363A (en) *	1982-01-25	1986-10-21	Ciba-Geigy Corporation	N-phenylsulfonyl-N'-triazinylureas
ZA836639B (en) *	1982-09-08	1984-05-30	Ciba Geigy Ag	Novel sulfonylureas
JPS6036386A (ja) *	1983-08-05	1985-02-25	東芝セラミツクス株式会社	スラデイングノズル用充填材
JP2546200B2 (ja) *	1991-02-20	1996-10-23	東ソー株式会社	田植前湛水下水田除草用水性懸濁製剤および散布方法
JP5468289B2 (ja) *	2008-04-18	2014-04-09	石原産業株式会社	ピリミジン系化合物の製造方法

1981
- 1981-03-05 PH PH25317A patent/PH17301A/en unknown
- 1981-03-05 ZA ZA00811484A patent/ZA811484B/xx unknown
- 1981-03-05 JP JP3063181A patent/JPS56139466A/ja active Pending
- 1981-03-05 CA CA000372421A patent/CA1189073A/fr not_active Expired
- 1981-03-07 KR KR1019810000751A patent/KR830005165A/ko not_active Ceased

Also Published As

Publication number	Publication date
PH17301A (en)	1984-07-18
JPS56139466A (en)	1981-10-30
KR830005165A (ko)	1983-08-03
ZA811484B (en)	1982-10-27

Legal Events

Date	Code	Title	Description
2002-06-18	MKEX	Expiry

Publication	Publication Date	Title
US4435206A (en)	1984-03-06	Agricultural pyridinesulfonamides
EP0120814B1 (fr)	1988-07-27	Urées N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl
CA1167847A (fr)	1984-05-22	Sulfonamides herbicides
EP0099339B1 (fr)	1987-01-07	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinylurées condensées
EP0035893B1 (fr)	1985-11-21	Dérivés de benzène- et pyridine-sulfonamides à activité herbicide
CA1159066A (fr)	1983-12-20	Sulfonamides herbicides
EP0102925B1 (fr)	1988-10-12	N-phénylsulfonyl-N'-pyrimidinyl- et -triazinylurées
CA1204112A (fr)	1986-05-06	Sulfonamides herbicides
EP0041404A2 (fr)	1981-12-09	Thiophènesulfonamides à activité herbicide
EP0044808A2 (fr)	1982-01-27	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinyl urées
CA1204113A (fr)	1986-05-06	Sulfonamides herbicides
EP0161211B1 (fr)	1990-08-01	N-hétérocyclosulfonyl N'-pyrimidinyl et triazinylurées
CA1157021A (fr)	1983-11-15	Urees et iso-urees pour l'agriculture
CA1225642A (fr)	1987-08-18	Sulfonamides herbicides
EP0128116B1 (fr)	1987-08-12	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinyl urées condensé
US4522645A (en)	1985-06-11	Agricultural pyridinesulfonamides
EP0073562B1 (fr)	1988-11-09	Urées triazoles à activité herbicide
NZ198841A (en)	1984-09-28	Benzylsulphonylurea derivatives
CA1221686A (fr)	1987-05-12	Sulfonamides herbicides
EP0082681A2 (fr)	1983-06-29	Sulfonamides herbicides
US4528024A (en)	1985-07-09	Herbicidal alkyl sulfones
CA1189073A (fr)	1985-06-18	Herbicides a base de pyridylsulfone
US4589909A (en)	1986-05-20	Benzofuran and benzothiophene sulfonamides
US4515624A (en)	1985-05-07	Herbicidal sulfonamides
US4425155A (en)	1984-01-10	Herbicidal sulfonamide N-oxides