CA1205077A - Derives de 3-isoxazolyl-2-imidazolidinone, herbicides - Google Patents

Derives de 3-isoxazolyl-2-imidazolidinone, herbicides

Info

Publication number: CA1205077A
Authority: CA; Canada
Prior art keywords: methyl; butyl; isoxazolyl; imidazolidinone; compound
Prior art date: 1983-03-28
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

CA000450478A

Other languages

English (en)

Inventor

Jay K. Rinehart

Muppala S. Raju

Jerome M. Lavanish

James A. Schwindeman

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.)

1983-03-28

Filing date

1984-03-26

Publication date

1986-05-27

1984-03-26 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1986-05-27 Application granted granted Critical

1986-05-27 Publication of CA1205077A publication Critical patent/CA1205077A/fr

Status Expired legal-status Critical Current

Links

QDAIYONGIKTEJS-UHFFFAOYSA-N 1-(1,2-oxazol-3-yl)imidazolidin-2-one Chemical class O=C1NCCN1C1=NOC=C1 QDAIYONGIKTEJS-UHFFFAOYSA-N 0.000 title abstract description 6
241000196324 Embryophyta Species 0.000 claims abstract description 34
-1 5-substituted-2-imidazolidinones Chemical class 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 64
230000002363 herbicidal effect Effects 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 16
239000004009 herbicide Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
238000000034 method Methods 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000001963 growth medium Substances 0.000 claims 8
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 claims 1
230000001473 noxious effect Effects 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
238000004458 analytical method Methods 0.000 description 33
238000010992 reflux Methods 0.000 description 28
239000002904 solvent Substances 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 24
238000002360 preparation method Methods 0.000 description 21
229940093499 ethyl acetate Drugs 0.000 description 20
235000019439 ethyl acetate Nutrition 0.000 description 20
239000000047 product Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
239000007858 starting material Substances 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
238000005984 hydrogenation reaction Methods 0.000 description 9
238000003760 magnetic stirring Methods 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
240000008100 Brassica rapa Species 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
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 6
240000000321 Abutilon grandifolium Species 0.000 description 6
235000011292 Brassica rapa Nutrition 0.000 description 6
235000004977 Brassica sinapistrum Nutrition 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
241000207890 Ipomoea purpurea Species 0.000 description 6
235000003403 Limnocharis flava Nutrition 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000006378 damage Effects 0.000 description 6
239000003480 eluent Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
235000007320 Avena fatua Nutrition 0.000 description 5
244000075850 Avena orientalis Species 0.000 description 5
244000298479 Cichorium intybus Species 0.000 description 5
235000007542 Cichorium intybus Nutrition 0.000 description 5
240000008853 Datura stramonium Species 0.000 description 5
235000010823 Digitaria sanguinalis Nutrition 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
235000002834 Sida rhombifolia Nutrition 0.000 description 5
240000003194 Sida rhombifolia Species 0.000 description 5
240000002439 Sorghum halepense Species 0.000 description 5
235000005373 Uvularia sessilifolia Nutrition 0.000 description 5
208000027418 Wounds and injury Diseases 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229960004132 diethyl ether Drugs 0.000 description 5
208000014674 injury Diseases 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
244000152970 Digitaria sanguinalis Species 0.000 description 4
244000058871 Echinochloa crus-galli Species 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
235000008515 Setaria glauca Nutrition 0.000 description 4
235000001155 Setaria leucopila Nutrition 0.000 description 4
244000010062 Setaria pumila Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000010502 orange oil Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 3
239000002689 soil Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
QGCGHXQDBJCWFG-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-ethoxy-1-methylimidazolidin-2-one Chemical compound C(C)(C)(C)C1=CC(=NO1)N1C(N(CC1OCC)C)=O QGCGHXQDBJCWFG-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
240000006122 Chenopodium album Species 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
240000003173 Drymaria cordata Species 0.000 description 2
244000025670 Eleusine indica Species 0.000 description 2
235000014716 Eleusine indica Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229940000425 combination drug Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000007921 spray Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
DFHPQWMZXDTXPW-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-4-(2,4-dichlorophenoxy)-5-hydroxy-3-methylimidazolidin-2-one Chemical compound C(C)(C)(C)C1=CC(=NO1)N1C(N(C(C1O)OC1=C(C=C(C=C1)Cl)Cl)C)=O DFHPQWMZXDTXPW-UHFFFAOYSA-N 0.000 description 1
ZFMKRNZPVOJKAJ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-5-hydroxy-4-methoxy-3-methylimidazolidin-2-one Chemical class C(C)(C)(C)C1=CC(=NO1)N1C(N(C(C1O)OC)C)=O ZFMKRNZPVOJKAJ-UHFFFAOYSA-N 0.000 description 1
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
YLQZHHXNPSEGBX-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-4-sulfanylimidazolidin-2-one Chemical compound C(C)(C)(C)C1=CC(=NO1)N1C(N(CC1S)C)=O YLQZHHXNPSEGBX-UHFFFAOYSA-N 0.000 description 1
BLKDSQFMVSGHOZ-UHFFFAOYSA-N 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-methoxy-1-methylimidazolidin-2-one Chemical compound COC1CN(C)C(=O)N1C1=NOC(C(C)(C)C)=C1 BLKDSQFMVSGHOZ-UHFFFAOYSA-N 0.000 description 1
OAFXSYIQHQGRNA-UHFFFAOYSA-N 4-amino-3-(5-tert-butyl-1,2-oxazol-3-yl)-1-methylimidazolidin-2-one Chemical compound O=C1N(C)CC(N)N1C1=NOC(C(C)(C)C)=C1 OAFXSYIQHQGRNA-UHFFFAOYSA-N 0.000 description 1
LMJDYCWAYWGSJD-UHFFFAOYSA-N 4-amino-3-(5-tert-butyl-1,2-oxazol-3-yl)-4-(2-hydroxyethyl)-1-methylimidazolidin-2-one Chemical compound C(C)(C)(C)C1=CC(=NO1)N1C(N(CC1(CCO)N)C)=O LMJDYCWAYWGSJD-UHFFFAOYSA-N 0.000 description 1
OPUQEOUHFJTSHA-UHFFFAOYSA-N 4-butylsulfanylimidazolidin-2-one Chemical compound CCCCSC1CNC(=O)N1 OPUQEOUHFJTSHA-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
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 1
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
244000036975 Ambrosia artemisiifolia Species 0.000 description 1
235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
240000005528 Arctium lappa Species 0.000 description 1
235000003130 Arctium lappa Nutrition 0.000 description 1
235000008078 Arctium minus Nutrition 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
240000008399 Barbarea vulgaris Species 0.000 description 1
235000007563 Barbarea vulgaris Nutrition 0.000 description 1
241001645380 Bassia scoparia Species 0.000 description 1
235000005637 Brassica campestris Nutrition 0.000 description 1
241001148727 Bromus tectorum Species 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N CH2-hydantoin Natural products O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
235000010301 Carolina horsenettle Nutrition 0.000 description 1
244000277285 Cassia obtusifolia Species 0.000 description 1
235000006719 Cassia obtusifolia Nutrition 0.000 description 1
235000014552 Cassia tora Nutrition 0.000 description 1
241000132585 Centaurea calcitrapa Species 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
235000005918 Cirsium arvense Nutrition 0.000 description 1
240000001579 Cirsium arvense Species 0.000 description 1
244000272323 Cirsium lanceolatum Species 0.000 description 1
235000010856 Cirsium lanceolatum Nutrition 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
244000075634 Cyperus rotundus Species 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 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
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
241000508725 Elymus repens Species 0.000 description 1
241000195955 Equisetum hyemale Species 0.000 description 1
241000490229 Eucephalus Species 0.000 description 1
244000207543 Euphorbia heterophylla Species 0.000 description 1
235000014820 Galium aparine Nutrition 0.000 description 1
241000169130 Heteranthera limosa Species 0.000 description 1
CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 1
235000017335 Hordeum vulgare subsp spontaneum Nutrition 0.000 description 1
241001299819 Hordeum vulgare subsp. spontaneum Species 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
241000209082 Lolium Species 0.000 description 1
241000083473 Lychnis Species 0.000 description 1
235000000060 Malva neglecta Nutrition 0.000 description 1
240000000982 Malva neglecta Species 0.000 description 1
235000012629 Mentha aquatica Nutrition 0.000 description 1
239000005583 Metribuzin Substances 0.000 description 1
235000009382 Mollugo verticillata Nutrition 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
241001465363 Panicum capillare Species 0.000 description 1
235000015225 Panicum colonum Nutrition 0.000 description 1
241001148659 Panicum dichotomiflorum Species 0.000 description 1
240000000275 Persicaria hydropiper Species 0.000 description 1
235000017337 Persicaria hydropiper Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
240000005218 Phyla nodiflora Species 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
244000292697 Polygonum aviculare Species 0.000 description 1
235000006386 Polygonum aviculare Nutrition 0.000 description 1
235000004442 Polygonum persicaria Nutrition 0.000 description 1
244000234609 Portulaca oleracea Species 0.000 description 1
235000001855 Portulaca oleracea Nutrition 0.000 description 1
241000756999 Potamogetonaceae Species 0.000 description 1
235000015422 Rumex crispus ssp. crispus Nutrition 0.000 description 1
235000015426 Rumex crispus ssp. fauriei Nutrition 0.000 description 1
244000207667 Rumex vesicarius Species 0.000 description 1
OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
244000275012 Sesbania cannabina Species 0.000 description 1
241000501039 Solanum carolinense Species 0.000 description 1
240000001949 Taraxacum officinale Species 0.000 description 1
235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
235000008214 Thlaspi arvense Nutrition 0.000 description 1
240000008488 Thlaspi arvense Species 0.000 description 1
240000000260 Typha latifolia Species 0.000 description 1
241000159750 Urtica cannabina Species 0.000 description 1
244000145469 Vernonia anthelmintica Species 0.000 description 1
235000013018 Vernonia anthelmintica Nutrition 0.000 description 1
244000067505 Xanthium strumarium Species 0.000 description 1
NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000003484 annual ragweed Nutrition 0.000 description 1
MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010310 bull nettle Nutrition 0.000 description 1
235000006263 bur ragweed Nutrition 0.000 description 1
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
235000003488 common ragweed Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
235000010313 devils tomato Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
NIDZUMSLERGAON-UHFFFAOYSA-N ethyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CCOC(=O)CNC NIDZUMSLERGAON-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000000727 fraction Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
PPVUCLAYECHOQZ-UHFFFAOYSA-N imidazolidine-4,5-dione Chemical compound O=C1NCNC1=O PPVUCLAYECHOQZ-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002386 leaching Methods 0.000 description 1
QENHCSSJTJWZAL-UHFFFAOYSA-N magnesium sulfide Chemical compound [Mg+2].[S-2] QENHCSSJTJWZAL-UHFFFAOYSA-N 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
102200035859 rs6138 Human genes 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000003971 tillage Methods 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA000450478A 1983-03-28 1984-03-26 Derives de 3-isoxazolyl-2-imidazolidinone, herbicides Expired CA1205077A (fr)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date
US47923283A	1983-03-28	1983-03-28
US479,232		1983-03-28
US49081983A	1983-05-02	1983-05-02
US490,819		1983-05-02
US49194983A	1983-05-05	1983-05-05
US491,949		1983-05-05
US55749283A	1983-12-02	1983-12-02
US557,492		1983-12-02

Publications (1)

Publication Number	Publication Date
CA1205077A true CA1205077A (fr)	1986-05-27

Family

ID=27504226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000450478A Expired CA1205077A (fr)	1983-03-28	1984-03-26	Derives de 3-isoxazolyl-2-imidazolidinone, herbicides

Country Status (3)

Country	Link
CA (1)	CA1205077A (fr)
FR (1)	FR2543552B1 (fr)
IT (1)	IT1178919B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2015193202A1 (fr) *	2014-06-16	2015-12-23	Syngenta Participations Ag	Composés herbicides
CN105873918A (zh) *	2013-12-23	2016-08-17	先正达参股股份有限公司	具有除草活性的二氢-乙内酰脲衍生物
WO2016162265A1 (fr) *	2015-04-07	2016-10-13	Syngenta Participations Ag	Mélanges herbicides
WO2018015476A1 (fr)	2016-07-22	2018-01-25	Syngenta Participations Ag	Procédé de lutte contre les nuisibles des végétaux
WO2018065311A1 (fr)	2016-10-07	2018-04-12	Syngenta Participations Ag	Mélanges herbicides
WO2018065309A1 (fr)	2016-10-07	2018-04-12	Syngenta Participations Ag	Mélanges herbicides
WO2020161147A1 (fr)	2019-02-05	2020-08-13	Syngenta Crop Protection Ag	Mélanges herbicides
WO2020164925A1 (fr)	2019-02-15	2020-08-20	Syngenta Crop Protection Ag	Compositions herbicides

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4659836A (en) *	1985-06-10	1987-04-21	Ppg Industries, Inc.	Imidazolidinone imines
AU581763B2 (en) *	1985-06-14	1989-03-02	Ppg Industries, Inc.	Herbicidal imidazolidinone derivatives
US4707180A (en) *	1985-06-14	1987-11-17	Ppg Industries, Inc.	Herbicidally active isoxazolyl-imidazolidinone derivatives
US4756744A (en) *	1985-06-24	1988-07-12	Ppg Industries, Inc.	Herbicidally active 4-aminoalkylamino-3-isoxazolyl-2-imidazolidinone derivatives
US5484763A (en) *	1995-02-10	1996-01-16	American Cyanamid Company	Substituted benzisoxazole and benzisothiazole herbicidal agents

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT73297B (en) *	1980-07-07	1982-09-06	Lilly Co Eli	Pocess for preparing isoxazolyimidazolidinone
US4354030A (en) *	1981-12-24	1982-10-12	Eli Lilly And Company	Isoxazolylimidazolidinone herbicides

1984
- 1984-03-26 CA CA000450478A patent/CA1205077A/fr not_active Expired
- 1984-03-27 IT IT67299/84A patent/IT1178919B/it active
- 1984-03-28 FR FR8404881A patent/FR2543552B1/fr not_active Expired

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105873918A (zh) *	2013-12-23	2016-08-17	先正达参股股份有限公司	具有除草活性的二氢-乙内酰脲衍生物
WO2015193202A1 (fr) *	2014-06-16	2015-12-23	Syngenta Participations Ag	Composés herbicides
WO2016162265A1 (fr) *	2015-04-07	2016-10-13	Syngenta Participations Ag	Mélanges herbicides
JP2018510896A (ja) *	2015-04-07	2018-04-19	シンジェンタパーティシペーションズアーゲー	除草性混合物
WO2018015476A1 (fr)	2016-07-22	2018-01-25	Syngenta Participations Ag	Procédé de lutte contre les nuisibles des végétaux
WO2018065311A1 (fr)	2016-10-07	2018-04-12	Syngenta Participations Ag	Mélanges herbicides
WO2018065309A1 (fr)	2016-10-07	2018-04-12	Syngenta Participations Ag	Mélanges herbicides
WO2020161147A1 (fr)	2019-02-05	2020-08-13	Syngenta Crop Protection Ag	Mélanges herbicides
WO2020164925A1 (fr)	2019-02-15	2020-08-20	Syngenta Crop Protection Ag	Compositions herbicides

Also Published As

Publication number	Publication date
IT8467299A1 (it)	1985-09-27
IT1178919B (it)	1987-09-16
FR2543552A1 (fr)	1984-10-05
IT8467299A0 (it)	1984-03-27
FR2543552B1 (fr)	1986-07-25

Legal Events

Date	Code	Title	Description
2004-03-26	MKEX	Expiry

Publication	Publication Date	Title
US4911754A (en)	1990-03-27	Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds
CA2023492A1 (fr)	1991-03-01	Glutarimides synthetiques
EP0726268A1 (fr)	1996-08-14	Benzisoxazoles et benzisothiazoles substitués et leur utilisation comme herbicides
CA1294283C (fr)	1992-01-14	Composes benzisoxazole ou benzisothiazole substitues, a activite herbicide
EP0264467B1 (fr)	1992-06-24	Dérivés sulfamoyl urées
US4622065A (en)	1986-11-11	Sulfamoyl urea derivatives
US4571255A (en)	1986-02-18	Subsituted phenoxybenzisoxazole herbicides
US4507145A (en)	1985-03-26	Herbicidal 3-[substituted 3- or 5-isoxazolyl]-1-4-, or 5-substituted-2-imidazolidinones
US4756744A (en)	1988-07-12	Herbicidally active 4-aminoalkylamino-3-isoxazolyl-2-imidazolidinone derivatives
US4717414A (en)	1988-01-05	Herbicidally active imidazopyrrolo-pyridine (or benzene) derivatives
US4696695A (en)	1987-09-29	Sulfamoyl urea derivatives
CA1211447A (fr)	1986-09-16	Derives de diphenylether-oxime-ester
US4741762A (en)	1988-05-03	Sulfamoyl urea derivatives
US4790868A (en)	1988-12-13	Herbicidally active substituted phenoxy or phenylthio benzoxazolone (or benzthiazolone) compounds
EP0184122B1 (fr)	1991-07-17	Dérivés sulfamoyl urées
US4592776A (en)	1986-06-03	Sulfamoyl urea derivatives
US4707180A (en)	1987-11-17	Herbicidally active isoxazolyl-imidazolidinone derivatives
US4666508A (en)	1987-05-19	Sulfamoyl urea derivatives
US4836845A (en)	1989-06-06	Herbicidally active isoxazolyl-imadazolidinone derivatives
US4746351A (en)	1988-05-24	Herbicidally active substituted phenoxy benzoxazole (or benzothiazole)
US4612038A (en)	1986-09-16	Herbicidally active 3-oxadiazolyl-2-imidazolidinones
US4596883A (en)	1986-06-24	Herbicidally active substituted diphenyl ethers
US4790870A (en)	1988-12-13	Herbicidally active aryloxy optionally oxo-substituted indane or tetralin derivatives
EP0205067A2 (fr)	1986-12-17	Dérivés d'imidazolidinone ayant une activité herbicide
US4602939A (en)	1986-07-29	Sulfamoyl urea derivatives