CA1131232A - Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees - Google Patents

Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees

Info

Publication number: CA1131232A
Authority: CA; Canada
Prior art keywords: grams; compound; pyridinyl; urea; compounds
Prior art date: 1978-08-31
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

CA384,189A

Other languages

English (en)

Inventor

Robert G. Suhr

John L. Miesel

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.)

Eli Lilly and Co

Original Assignee

Eli Lilly 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.)

1978-08-31

Filing date

1981-08-19

Publication date

1982-09-07

1979-07-19 Priority claimed from CA332,130A external-priority patent/CA1128044A/fr

1981-08-19 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1981-08-19 Priority to CA384,189A priority Critical patent/CA1131232A/fr

1982-09-07 Application granted granted Critical

1982-09-07 Publication of CA1131232A publication Critical patent/CA1131232A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 41
235000013877 carbamide Nutrition 0.000 title description 5
150000003672 ureas Chemical class 0.000 title description 2
-1 chloro, fluoro, methyl Chemical group 0.000 claims abstract description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
241000238631 Hexapoda Species 0.000 claims description 19
238000000034 method Methods 0.000 claims description 19
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241000255925 Diptera Species 0.000 claims description 3
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239000013543 active substance Substances 0.000 claims description 3
ZIAFLWORIYLPPF-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(3,5-dimethoxyphenoxy)pyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC(OC)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 ZIAFLWORIYLPPF-UHFFFAOYSA-N 0.000 claims 2
KKHKVMFGIACBNN-UHFFFAOYSA-N 2-chloro-n-[[6-(3,5-dimethoxyphenoxy)pyridin-3-yl]carbamoyl]-6-methoxybenzamide Chemical compound COC1=CC(OC)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)OC)=CC=2)=C1 KKHKVMFGIACBNN-UHFFFAOYSA-N 0.000 claims 1
241000238814 Orthoptera Species 0.000 claims 1
RXZXRWAVJKWYDH-UHFFFAOYSA-N n-[[6-(3,5-dimethoxyphenoxy)pyridin-3-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound COC1=CC(OC)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 RXZXRWAVJKWYDH-UHFFFAOYSA-N 0.000 claims 1
OPOBGGACLYCTAH-UHFFFAOYSA-N n-[[6-(3,5-dimethoxyphenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3OC)OC)=CC=2)=C1 OPOBGGACLYCTAH-UHFFFAOYSA-N 0.000 claims 1
CICIRLWUEDLACG-UHFFFAOYSA-N n-[[6-(3,5-dimethoxyphenoxy)pyridin-3-yl]carbamoyl]-2-fluoro-6-methoxybenzamide Chemical compound COC1=CC(OC)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3F)OC)=CC=2)=C1 CICIRLWUEDLACG-UHFFFAOYSA-N 0.000 claims 1
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241000254112 Tribolium confusum Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
241000766025 Vitacea polistiformis Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
241001136529 Zeugodacus cucurbitae Species 0.000 description 1
241000314934 Zygogramma exclamationis Species 0.000 description 1
HEDLQLRXJIQDGS-UHFFFAOYSA-N [Br].NC1=NC=C(C=C1)Br Chemical compound [Br].NC1=NC=C(C=C1)Br HEDLQLRXJIQDGS-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical class Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003570 air Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004891 communication Methods 0.000 description 1
230000006854 communication Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
SQEDZTDNVYVPQL-UHFFFAOYSA-N dodecylbenzene;sodium Chemical compound [Na].CCCCCCCCCCCCC1=CC=CC=C1 SQEDZTDNVYVPQL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical class CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000010871 livestock manure Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
235000019333 sodium laurylsulphate 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
241000894007 species Species 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001629 suppression Effects 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)

CA384,189A 1978-08-31 1981-08-19 Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees Expired CA1131232A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA384,189A CA1131232A (fr)	1978-08-31	1981-08-19	Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US93872178A	1978-08-31	1978-08-31
US938,721		1978-08-31
CA332,130A CA1128044A (fr)	1978-08-31	1979-07-19	1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees
CA384,189A CA1131232A (fr)	1978-08-31	1981-08-19	Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees

Publications (1)

Publication Number	Publication Date
CA1131232A true CA1131232A (fr)	1982-09-07

Family

ID=27166335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA384,189A Expired CA1131232A (fr)	1978-08-31	1981-08-19	Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees

Country Status (1)

Country	Link
CA (1)	CA1131232A (fr)

1981
- 1981-08-19 CA CA384,189A patent/CA1131232A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-09-07	MKEX	Expiry

Publication	Publication Date	Title
US4063928A (en)	1977-12-20	Composition and method of controlling undesired plant growth with substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives
RU2140739C1 (ru)	1999-11-10	Способ подавления роста нежелательной растительности, замещенные гетероциклами пиридины, способы их получения и гербицидная композиция
DD215461A5 (de)	1984-11-14	Herbizides und den pflanzenwuchs hemmendes mittel
EP0042732A1 (fr)	1981-12-30	1-Benzoyl-urées et thiourées substituées en position 3, leur préparation, compositions insecticides les contenant et leur utilisation comme insecticides
US4264605A (en)	1981-04-28	1-Benzoyl-3-(aryloxy- or arylthiopyridinyl) urea compounds
US4293552A (en)	1981-10-06	Novel 1-(mono-o-substituted benzoyl)-3-(substituted pyrazinyl) ureas
US4003734A (en)	1977-01-18	Substituted pyridinyloxy(thio)phenyl-acetamides, -ureas and urea derivatives and herbicidal compositions and methods containing said compounds
EP0008881A1 (fr)	1980-03-19	1-Benzoyl-3-pyridinyl urées, leur utilisation comme insecticides, leur préparation et compositions les contenant
US4173639A (en)	1979-11-06	1-Benzoyl-3-(alkoxy- or alkylthiopyridinyl)ureas
US4219557A (en)	1980-08-26	1-(2,6-Dihalobenzoyl)-3-(5-substituted-2-pyridinyl)urea compounds and insecticidal use
CA1131232A (fr)	1982-09-07	Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees
US4003733A (en)	1977-01-18	Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives
US4540578A (en)	1985-09-10	Pesticidal phenoxypyridyl benzoyl ureas
US4518804A (en)	1985-05-21	Halo(alkoxy/alkylthio)-benzenamines
JPS6245228B2 (fr)	1987-09-25
US4030910A (en)	1977-06-21	Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives, herbicidal compositions and methods containing same
US4521426A (en)	1985-06-04	Pesticidal bicyclooxyheterocyclyl aroyl ureas
US4602109A (en)	1986-07-22	Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation
KR830002348B1 (ko)	1983-10-24	1-벤조일-3-피리디닐 우레아화합물의 제조방법
EP0115210B1 (fr)	1988-05-11	Benzoyl uréas à activité pesticide et procédé pour leur préparation
CA1128044A (fr)	1982-07-20	1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees
US4366155A (en)	1982-12-28	1-Benzoyl-3-(6-oxopyridazinyl)ureas, compositions, and insecticidal method
US4174209A (en)	1979-11-13	Herbicidal 1-alkyl-3-phenylpyridinium salts
KR0185125B1 (ko)	1999-05-15	(4-벤조일 우레이도)벤조일우레아 유도체와 이의 제조방법 및 이를 함유하는 농약 조성물
US4026937A (en)	1977-05-31	Substituted pyridinylalkoxy-, pyridinylalkylsulfonyl- and pyridinylalkylthio-phenylureas