CA1105033A - Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent. - Google Patents

Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent.

Info

Publication number: CA1105033A
Authority: CA; Canada
Prior art keywords: butyl; isoxazolyl; compound; namely; hydrogen
Prior art date: 1978-07-07
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

CA307,010A

Other languages

English (en)

Inventor

Hisajiro Yukinaga

Shinzaburo Sumimoto

Ichiro Ishizuka

Jitsuo Sugita

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.)

Shionogi and Co Ltd

Original Assignee

Shionogi and Co Ltd

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.)

1978-07-07

Filing date

1978-07-07

Publication date

1981-07-14

1978-07-07 Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd

1978-07-07 Priority to CA307,010A priority Critical patent/CA1105033A/fr

1981-07-14 Application granted granted Critical

1981-07-14 Publication of CA1105033A publication Critical patent/CA1105033A/fr

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title abstract description 17
239000000203 mixture Substances 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 34
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
229910052736 halogen Chemical group 0.000 claims abstract description 8
150000002367 halogens Chemical group 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 5
BDLVSEWUCZQDTD-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)propanamide Chemical compound CCC(=O)NC=1C=C(C(C)(C)C)ON=1 BDLVSEWUCZQDTD-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 2
229950001902 dimevamide Drugs 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
SIPKOMRKJGMRLM-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 SIPKOMRKJGMRLM-UHFFFAOYSA-N 0.000 claims description 2
RNANTPNODFUWMF-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-n-methylcyclopropanecarboxamide Chemical compound C1=C(C(C)(C)C)ON=C1N(C)C(=O)C1CC1 RNANTPNODFUWMF-UHFFFAOYSA-N 0.000 claims description 2
GTRMBJUHULQLKN-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)hexanamide Chemical compound CCCCCC(=O)NC=1C=C(C(C)(C)C)ON=1 GTRMBJUHULQLKN-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
PIDSYFQDPBSVTA-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-methylhexanamide Chemical compound CCCCC(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 PIDSYFQDPBSVTA-UHFFFAOYSA-N 0.000 claims 1
ZEYARATZVOFFLN-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-methylpentanamide Chemical compound CCCC(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 ZEYARATZVOFFLN-UHFFFAOYSA-N 0.000 claims 1
SSCBEUWAMORONB-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)cyclopropanecarboxamide Chemical compound O1C(C(C)(C)C)=CC(NC(=O)C2CC2)=N1 SSCBEUWAMORONB-UHFFFAOYSA-N 0.000 claims 1
AKBNMHQBJZLAAP-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)pentanamide Chemical compound CCCCC(=O)NC=1C=C(C(C)(C)C)ON=1 AKBNMHQBJZLAAP-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000004009 herbicide Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
BSEXNZMHLUMQKR-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1.NC(=O)C1CC1 BSEXNZMHLUMQKR-UHFFFAOYSA-N 0.000 description 5
150000002545 isoxazoles Chemical class 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
235000003990 Monochoria hastata Nutrition 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000192043 Echinochloa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000169139 Monochoria Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000004927 clay Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
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 2
235000005637 Brassica campestris Nutrition 0.000 description 2
241001301148 Brassica rapa subsp. oleifera Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
-1 butyl Chemical group 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
230000000875 corresponding effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229940047889 isobutyramide Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
MSIJLVMSKDXAQN-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]-4-methylpiperazine;hydron;chloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 MSIJLVMSKDXAQN-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SIMLCFANWCDGAF-UHFFFAOYSA-N 3-methylpentanamide Chemical compound CCC(C)CC(N)=O SIMLCFANWCDGAF-UHFFFAOYSA-N 0.000 description 1
241000219318 Amaranthus Species 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
206010008428 Chemical poisoning Diseases 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
244000000626 Daucus carota Species 0.000 description 1
235000002767 Daucus carota Nutrition 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
244000017020 Ipomoea batatas Species 0.000 description 1
235000002678 Ipomoea batatas Nutrition 0.000 description 1
235000014435 Mentha Nutrition 0.000 description 1
241001072983 Mentha Species 0.000 description 1
240000000178 Monochoria vaginalis Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000276568 Oryzias Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
235000010582 Pisum sativum Nutrition 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
241000205407 Polygonum Species 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
240000000111 Saccharum officinarum Species 0.000 description 1
235000007201 Saccharum officinarum Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
244000061458 Solanum melongena Species 0.000 description 1
235000002597 Solanum melongena Nutrition 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
241000358324 Viverricula indica 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
239000002671 adjuvant Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000009332 manuring Methods 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
IZUPBVBPLAPZRR-UHFFFAOYSA-M pentachlorophenolate Chemical compound [O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-M 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA307,010A 1978-07-07 1978-07-07 Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent. Expired CA1105033A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA307,010A CA1105033A (fr)	1978-07-07	1978-07-07	Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA307,010A CA1105033A (fr)	1978-07-07	1978-07-07	Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent.

Publications (1)

Publication Number	Publication Date
CA1105033A true CA1105033A (fr)	1981-07-14

Family

ID=4111858

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,010A Expired CA1105033A (fr)	1978-07-07	1978-07-07	Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent.

Country Status (1)

Country	Link
CA (1)	CA1105033A (fr)

1978
- 1978-07-07 CA CA307,010A patent/CA1105033A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-07-14	MKEX	Expiry

Publication	Publication Date	Title
US4293328A (en)	1981-10-06	N-(5-t-Butyl-3-isoxazolyl)alkanamide derivatives and herbicidal compositions containing them
CA1164869A (fr)	1984-04-03	Agents pour proteger les cultures
BR9905766B1 (pt)	2010-11-30	derivado de ftalamida, insetidida agro-hortìcula, e, processo para a utilização do mesmo.
GB1590870A (en)	1981-06-10	N-(5-t-butyl-3-isoxazolyl) alkanamide derivatives having herbicidal activity
EP0144098A1 (fr)	1985-06-12	Urées cycliques d'isoxazole
KR0147844B1 (ko)	1998-08-17	환상 아미드 유도체 및 제초체
GB1574477A (en)	1980-09-10	Benzenesulphonamide derivatives and their use as herbicide
EP0197495B1 (fr)	1990-07-11	Dérivés de 4,5,6,7-tétrahydro-2H-indazole et herbicides les contenant
CA2021919A1 (fr)	1991-01-27	Derives substitues en 5 de la 1,3,4-thiadiazole, leur preparation et leur utilisation comme pesticides
JPS5810361B2 (ja)	1983-02-25	３−アルチルイソオキサゾ−ル系除草剤
GB2043062A (en)	1980-10-01	N-(heterocyclyl)-acetanilide derivatives and herbicidal and plant growth regulating compositions containing them
US4501746A (en)	1985-02-26	N,N-disubstituted carboxamide derivatives, and fungicidal use thereof
CA1105033A (fr)	1981-07-14	Derives de n-(5-t-butyl-3-isoxazolyl) alcanamides et substances herbicides qui en contiennent.
EP0271975B1 (fr)	1992-06-24	Dérivés d'acide 3-perfluoroalkyl-isoxazol-5-yl-oxycarboxylique, procédés pour leur préparation et leur utilisation comme herbicides
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