JPS6145980B2 - - Google Patents

Info

Publication number

JPS6145980B2

JPS6145980B2 JP2671479A JP2671479A JPS6145980B2 JP S6145980 B2 JPS6145980 B2 JP S6145980B2 JP 2671479 A JP2671479 A JP 2671479A JP 2671479 A JP2671479 A JP 2671479A JP S6145980 B2 JPS6145980 B2 JP S6145980B2

Authority

JP

Japan

Prior art keywords

formula

compound

group

phenyl

present

Prior art date

1979-03-09

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

Links

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• 150000001875 compounds Chemical class 0.000 claims description 22
• 239000004009 herbicide Substances 0.000 claims description 18
• 239000004480 active ingredient Substances 0.000 claims description 13
• 230000002363 herbicidal effect Effects 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000003839 salts Chemical class 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• -1 alcoholate Chemical compound 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• 241000196324 Embryophyta Species 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• 239000002689 soil Substances 0.000 description 8
• 230000035784 germination Effects 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 230000012010 growth Effects 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
• 235000017898 Digitaria ciliaris Nutrition 0.000 description 4
• 235000005476 Digitaria cruciata Nutrition 0.000 description 4
• 235000006830 Digitaria didactyla Nutrition 0.000 description 4
• 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
• 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
• 244000025670 Eleusine indica Species 0.000 description 4
• 235000014716 Eleusine indica Nutrition 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000004094 surface-active agent Substances 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 235000007319 Avena orientalis Nutrition 0.000 description 3
• 241000209763 Avena sativa Species 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 244000068988 Glycine max Species 0.000 description 3
• 235000010469 Glycine max Nutrition 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 240000007594 Oryza sativa Species 0.000 description 3
• 235000007164 Oryza sativa Nutrition 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
• 239000002253 acid Substances 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 235000009566 rice Nutrition 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
• 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
• 244000055702 Amaranthus viridis Species 0.000 description 2
• 235000004135 Amaranthus viridis Nutrition 0.000 description 2
• 235000007558 Avena sp Nutrition 0.000 description 2
• 235000016068 Berberis vulgaris Nutrition 0.000 description 2
• 241000335053 Beta vulgaris Species 0.000 description 2
• 235000009344 Chenopodium album Nutrition 0.000 description 2
• 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
• 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
• 239000005909 Kieselgur Substances 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 235000006089 Phaseolus angularis Nutrition 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 244000197975 Solidago virgaurea Species 0.000 description 2
• 235000000914 Solidago virgaurea Nutrition 0.000 description 2
• 240000007098 Vigna angularis Species 0.000 description 2
• 235000010711 Vigna angularis Nutrition 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 239000007864 aqueous solution 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
• 239000000969 carrier Substances 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
• 238000007865 diluting Methods 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 230000000887 hydrating effect Effects 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• VJLYHTOSFSGXGH-CQSZACIVSA-N (2R)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]pyrrolidine-2-carboxylic acid Chemical group NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2[C@H](CCC2)C(=O)O)C=CC=1 VJLYHTOSFSGXGH-CQSZACIVSA-N 0.000 description 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
• QGONIKZRWOOHBB-UHFFFAOYSA-N 2-propan-2-ylsulfanylethanol Chemical compound CC(C)SCCO QGONIKZRWOOHBB-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• YTAPFCPYBCQLEM-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)anilino]phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O YTAPFCPYBCQLEM-UHFFFAOYSA-N 0.000 description 1
• 241000254032 Acrididae Species 0.000 description 1
• 241000251468 Actinopterygii Species 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
• 244000067456 Chrysanthemum coronarium Species 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 244000058871 Echinochloa crus-galli Species 0.000 description 1
• 238000005481 NMR spectroscopy Methods 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 244000088415 Raphanus sativus Species 0.000 description 1
• 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
• 244000062793 Sorghum vulgare Species 0.000 description 1
• 244000300264 Spinacia oleracea Species 0.000 description 1
• 235000009337 Spinacia oleracea Nutrition 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 230000000895 acaricidal effect Effects 0.000 description 1
• 239000000642 acaricide Substances 0.000 description 1
• 230000007059 acute toxicity Effects 0.000 description 1
• 231100000403 acute toxicity Toxicity 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000003899 bactericide agent Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 229910052570 clay Inorganic materials 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 229940125797 compound 12 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 235000015134 garland chrysanthemum Nutrition 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 238000002329 infrared spectrum Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 239000002917 insecticide Substances 0.000 description 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
• 239000003350 kerosene Substances 0.000 description 1
• 244000144972 livestock Species 0.000 description 1
• 235000019713 millet Nutrition 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 239000005648 plant growth regulator Substances 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 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
• 235000019260 propionic acid Nutrition 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000010992 reflux Methods 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
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• 238000004381 surface treatment Methods 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 239000004563 wettable powder Substances 0.000 description 1