CA1221972A - 3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones - Google Patents

3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones

Info

Publication number: CA1221972A
Authority: CA; Canada
Prior art keywords: alkyl; carbon atoms; isoxazolyl; dimethylethyl; substituted
Prior art date: 1980-02-19
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

CA000506137A

Other languages

English (en)

Inventor

Jerome M. Lavanish

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.)

BASF SE

PPG Industries Inc

Original Assignee

PPG Industries Inc

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.)

1980-02-19

Filing date

1986-04-08

Publication date

1987-05-19

1980-02-19 Priority claimed from US06/122,633 external-priority patent/US4268679A/en

1980-11-18 Priority claimed from US06/207,151 external-priority patent/US4507145A/en

1986-04-08 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1986-04-08 Priority to CA000506137A priority Critical patent/CA1221972A/fr

1987-05-19 Application granted granted Critical

1987-05-19 Publication of CA1221972A publication Critical patent/CA1221972A/fr

Status Expired legal-status Critical Current

Links

-1 5- substituted-2-imidazolidinones Chemical class 0.000 title claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 15
239000004202 carbamide Substances 0.000 claims abstract description 15
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 11
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
150000001875 compounds Chemical class 0.000 abstract description 46
241000196324 Embryophyta Species 0.000 abstract description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 15
238000002360 preparation method Methods 0.000 abstract description 11
238000000034 method Methods 0.000 abstract description 9
230000002363 herbicidal effect Effects 0.000 abstract description 5
125000003342 alkenyl group Chemical group 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000013078 crystal Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
229960000443 hydrochloric acid Drugs 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000009472 formulation Methods 0.000 description 5
SCFGLMLXZAQXGC-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one Chemical compound O=C1N(C)CC(O)N1C1=NOC(C(C)(C)C)=C1 SCFGLMLXZAQXGC-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
229940015043 glyoxal Drugs 0.000 description 3
239000001963 growth medium Substances 0.000 description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000003760 magnetic stirring Methods 0.000 description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
SCMVCKIBKAYNGT-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-methylurea Chemical compound CNC(=O)NC1=CC(C(C)(C)C)=NO1 SCMVCKIBKAYNGT-UHFFFAOYSA-N 0.000 description 2
GUGLRTKPJBGNAF-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-methylurea Chemical compound CNC(=O)NC=1C=C(C(C)(C)C)ON=1 GUGLRTKPJBGNAF-UHFFFAOYSA-N 0.000 description 2
XAEAEFQXDBCTPL-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-4,5-dihydroxy-3-methylimidazolidin-2-one Chemical compound O=C1N(C)C(O)C(O)N1C1=NOC(C(C)(C)C)=C1 XAEAEFQXDBCTPL-UHFFFAOYSA-N 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
IQMVRIMSTBTDLV-UHFFFAOYSA-N 5-tert-butyl-3-isocyanato-1,2-oxazole Chemical compound CC(C)(C)C1=CC(N=C=O)=NO1 IQMVRIMSTBTDLV-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000002253 acid Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000306 component Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical class NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 description 1
HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 1
LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical class NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 1
150000008625 2-imidazolidinones Chemical class 0.000 description 1
LNQCKWNJBQNZRL-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-1-(2,2-dimethoxyethyl)-1-methylurea Chemical compound COC(OC)CN(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 LNQCKWNJBQNZRL-UHFFFAOYSA-N 0.000 description 1
APHNQOGPYLTSFX-UHFFFAOYSA-N 3-tert-butyl-1,2-oxazol-5-amine Chemical compound CC(C)(C)C=1C=C(N)ON=1 APHNQOGPYLTSFX-UHFFFAOYSA-N 0.000 description 1
PZGRYCFWQQTRNF-UHFFFAOYSA-N 4-hydroxy-1-methylimidazolidin-2-one Chemical compound CN1CC(O)NC1=O PZGRYCFWQQTRNF-UHFFFAOYSA-N 0.000 description 1
OYQNSKXKPTVURJ-UHFFFAOYSA-N 4-hydroxyimidazolidin-2-one Chemical class OC1CNC(=O)N1 OYQNSKXKPTVURJ-UHFFFAOYSA-N 0.000 description 1
GGXGVZJHUKEJHO-UHFFFAOYSA-N 5-tert-butyl-1,2-oxazol-3-amine Chemical compound CC(C)(C)C1=CC(N)=NO1 GGXGVZJHUKEJHO-UHFFFAOYSA-N 0.000 description 1
240000000321 Abutilon grandifolium Species 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
235000011292 Brassica rapa Nutrition 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
244000298479 Cichorium intybus Species 0.000 description 1
235000007542 Cichorium intybus Nutrition 0.000 description 1
240000008853 Datura stramonium Species 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
240000003176 Digitaria ciliaris Species 0.000 description 1
235000017898 Digitaria ciliaris Nutrition 0.000 description 1
235000005476 Digitaria cruciata Nutrition 0.000 description 1
235000006830 Digitaria didactyla Nutrition 0.000 description 1
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
244000058871 Echinochloa crus-galli Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
240000001549 Ipomoea eriocarpa Species 0.000 description 1
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
235000003403 Limnocharis flava Nutrition 0.000 description 1
VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
235000008515 Setaria glauca Nutrition 0.000 description 1
235000001155 Setaria leucopila Nutrition 0.000 description 1
244000010062 Setaria pumila Species 0.000 description 1
240000003194 Sida rhombifolia Species 0.000 description 1
235000002834 Sida rhombifolia Nutrition 0.000 description 1
240000002439 Sorghum halepense Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
YTXQBZYUDCMSRJ-UHFFFAOYSA-N [3-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-2-oxoimidazolidin-4-yl] benzoate Chemical compound C1=C(C(C)(C)C)ON=C1N1C(=O)N(C)CC1OC(=O)C1=CC=CC=C1 YTXQBZYUDCMSRJ-UHFFFAOYSA-N 0.000 description 1
UTDKHFWCFQKZLD-UHFFFAOYSA-N [3-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-2-oxoimidazolidin-4-yl] butanoate Chemical compound CCCC(=O)OC1CN(C)C(=O)N1C1=NOC(C(C)(C)C)=C1 UTDKHFWCFQKZLD-UHFFFAOYSA-N 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
244000209130 tickweed Species 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA000506137A 1980-02-19 1986-04-08 3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones Expired CA1221972A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000506137A CA1221972A (fr)	1980-02-19	1986-04-08	3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US122,633		1980-02-19
US06/122,633 US4268679A (en)	1980-02-19	1980-02-19	3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones
US207,151		1980-11-18
US06/207,151 US4507145A (en)	1980-02-19	1980-11-18	Herbicidal 3-[substituted 3- or 5-isoxazolyl]-1-4-, or 5-substituted-2-imidazolidinones
CA000371136A CA1215988A (fr)	1980-02-19	1981-02-18	3-[substitues 3- ou 5- isoxazolyl]-1-4, ou 5- substitue-2-imidazolidiones
CA000506137A CA1221972A (fr)	1980-02-19	1986-04-08	3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000371136A Division CA1215988A (fr)	1980-02-19	1981-02-18	3-[substitues 3- ou 5- isoxazolyl]-1-4, ou 5- substitue-2-imidazolidiones

Publications (1)

Publication Number	Publication Date
CA1221972A true CA1221972A (fr)	1987-05-19

Family

ID=27166969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000506137A Expired CA1221972A (fr)	1980-02-19	1986-04-08	3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones

Country Status (1)

Country	Link
CA (1)	CA1221972A (fr)

1986
- 1986-04-08 CA CA000506137A patent/CA1221972A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-05-19	MKEX	Expiry

Publication	Publication Date	Title
JPS6330913B2 (fr)	1988-06-21
EP0034456B1 (fr)	1984-08-15	3-(Isoxazolyl-3 ou 5 substitué) 2-imidazolidinones 1,4 ou 5 substitués, procédés pour leur préparation, compositions les contenant et leur utilisation comme herbicides
US4426527A (en)	1984-01-17	3-[5- Or 3-substituted-1,2,4-oxadiazol-3- or -5-yl]-1-substituted-4-substituted-5-substituted or unsubstituted-2-imidazolidinones
KR100291874B1 (ko)	2001-09-17	아미노피리미딘유도체및그의제조방법과용도
EP0044185A2 (fr)	1982-01-20	Dérivés d'imidazolidinone
KR20010100825A (ko)	2001-11-14	제초성 벤조일옥시 카르복실레이트 및 카르복스아마이드
CA1221972A (fr)	1987-05-19	3-[3- ou 5-isoxazolyle substitue]-1-4, ou 5- substituant-2-imidazolidinones
US4756744A (en)	1988-07-12	Herbicidally active 4-aminoalkylamino-3-isoxazolyl-2-imidazolidinone derivatives
SE441091B (sv)	1985-09-09	Substituerade difenyletrar, herbieidisk komposition innehallande dessa foreningar samt foreningarnas anvendning for kontroll av ogrestillvext
US4529435A (en)	1985-07-16	Herbicidally active isoxazol acetal ureas
US4911749A (en)	1990-03-27	Aquatic herbicidal methods
EP0427445B1 (fr)	1994-06-08	Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides
US4596883A (en)	1986-06-24	Herbicidally active substituted diphenyl ethers
US4863504A (en)	1989-09-05	Cyclohexadione derivatives, selective herbicidal compositions as well as herbicidal method
US4842640A (en)	1989-06-27	Oxadiazolone derivative, production process thereof, and herbicide containing same
EP0169521A2 (fr)	1986-01-29	Dérivés de cyclohexénone, procédé de préparation et utilisation dans la lutte contre les plantes indésirables
US4857099A (en)	1989-08-15	Terrestrial and aquatic herbicidal methods
US4314842A (en)	1982-02-09	Herbicidal substituted 1,3,4-thiadiazol-2-yl-4-hydroxy-1-methyl-2-imidazolidinones
US4430114A (en)	1984-02-07	2,6-Dinitroaniline herbicides, and use thereof
EP0128232B1 (fr)	1987-04-29	3-(5- Ou 3-substitué-1,2,4-oxadiazole-3- ou -5-yl)-1-substitué-4-substitué-5-substitué ou non-substitué-2-imidazolidinones
US4288243A (en)	1981-09-08	2',5'-Dioxo-1'-pyrrolydinyl 5-(2-halo-4-trifluoromethylphenoxy)-2-halo-, cyano- or nitrobenzoates
US4456466A (en)	1984-06-26	Herbicidally active benzoxazolyl acetophenone oxime derivatives
US4746351A (en)	1988-05-24	Herbicidally active substituted phenoxy benzoxazole (or benzothiazole)
US4836845A (en)	1989-06-06	Herbicidally active isoxazolyl-imadazolidinone derivatives
US4564385A (en)	1986-01-14	Herbicidally active substituted diphenyl ether oxime derivatives