IE44673B1 - Herbicidally active diurethanes,process for their manufacture and their use - Google Patents
Herbicidally active diurethanes,process for their manufacture and their useInfo
- Publication number
- IE44673B1 IE44673B1 IE273776A IE273776A IE44673B1 IE 44673 B1 IE44673 B1 IE 44673B1 IE 273776 A IE273776 A IE 273776A IE 273776 A IE273776 A IE 273776A IE 44673 B1 IE44673 B1 IE 44673B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- ester
- phenyl
- acid
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 91
- -1 trifluoromethylphenyl Chemical group 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 58
- 230000002363 herbicidal effect Effects 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- 244000061456 Solanum tuberosum Species 0.000 claims description 18
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 18
- 240000008042 Zea mays Species 0.000 claims description 17
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 17
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 17
- 235000009973 maize Nutrition 0.000 claims description 17
- 241000196324 Embryophyta Species 0.000 claims description 16
- 241000209140 Triticum Species 0.000 claims description 16
- 235000021307 Triticum Nutrition 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000007530 organic bases Chemical group 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- IEJBEBRAATYCNM-UHFFFAOYSA-N 2-bromoethyl(phenyl)carbamic acid Chemical compound BrCCN(C(=O)O)C1=CC=CC=C1 IEJBEBRAATYCNM-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 235000013339 cereals Nutrition 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- YJAWOJQCCHHOCT-UHFFFAOYSA-N 2-bromoethyl-(3-chlorophenyl)carbamic acid Chemical compound OC(=O)N(CCBr)C1=CC=CC(Cl)=C1 YJAWOJQCCHHOCT-UHFFFAOYSA-N 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- IXALHCKZWWWSOH-UHFFFAOYSA-N 2-chloroethyl-[3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)N(CCCl)C1=CC=CC(=C1)C(F)(F)F IXALHCKZWWWSOH-UHFFFAOYSA-N 0.000 claims description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims 1
- 235000007340 Hordeum vulgare Nutrition 0.000 claims 1
- SHRZYQVETAOHHI-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] n-(2-bromoethyl)-n-(3-chlorophenyl)carbamate Chemical compound CC(C)COC(=O)NC1=CC=CC(OC(=O)N(CCBr)C=2C=C(Cl)C=CC=2)=C1 SHRZYQVETAOHHI-UHFFFAOYSA-N 0.000 claims 1
- MUZGJCJTOMPYSY-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] n-(2-bromoethyl)-n-phenylcarbamate Chemical compound CC(=S)NC1=CC=CC(OC(=O)N(CCBr)C=2C=CC=CC=2)=C1 MUZGJCJTOMPYSY-UHFFFAOYSA-N 0.000 claims 1
- JZDVBUBDVCNMQX-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] n-(2-bromoethyl)-n-phenylcarbamate Chemical compound CCC(=S)NC1=CC=CC(OC(=O)N(CCBr)C=2C=CC=CC=2)=C1 JZDVBUBDVCNMQX-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 235000005775 Setaria Nutrition 0.000 description 17
- 241000232088 Setaria <nematode> Species 0.000 description 17
- 239000013543 active substance Substances 0.000 description 17
- 235000012015 potatoes Nutrition 0.000 description 17
- 241000743985 Alopecurus Species 0.000 description 16
- 241000205407 Polygonum Species 0.000 description 16
- 241000219318 Amaranthus Species 0.000 description 15
- 241000723353 Chrysanthemum Species 0.000 description 15
- 235000007516 Chrysanthemum Nutrition 0.000 description 15
- 235000017896 Digitaria Nutrition 0.000 description 15
- 241001303487 Digitaria <clam> Species 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 241001101998 Galium Species 0.000 description 15
- 241000209048 Poa Species 0.000 description 15
- 241000780602 Senecio Species 0.000 description 15
- 240000006694 Stellaria media Species 0.000 description 15
- 241000132570 Centaurea Species 0.000 description 14
- 241000192043 Echinochloa Species 0.000 description 14
- 241000520028 Lamium Species 0.000 description 14
- 235000005781 Avena Nutrition 0.000 description 13
- 241000209761 Avena Species 0.000 description 13
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KZGYVRNLURIQGF-UHFFFAOYSA-N 2-chloroethyl-(3-chlorophenyl)carbamic acid Chemical compound ClCCN(C(=O)O)C1=CC=CC(Cl)=C1 KZGYVRNLURIQGF-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 3
- 235000014820 Galium aparine Nutrition 0.000 description 3
- 101000760663 Hololena curta Mu-agatoxin-Hc1a Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 2
- ZAMRCGQXJHTHHA-UHFFFAOYSA-N 2-chloroethyl(phenyl)carbamic acid Chemical compound ClCCN(C(=O)O)C1=CC=CC=C1 ZAMRCGQXJHTHHA-UHFFFAOYSA-N 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 244000292693 Poa annua Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- RLWXCMXUNWHDRU-UHFFFAOYSA-N (3-methylphenyl)-(2-methylpropyl)carbamic acid Chemical compound CC(C)CN(C(O)=O)C1=CC=CC(C)=C1 RLWXCMXUNWHDRU-UHFFFAOYSA-N 0.000 description 1
- AVNCAFPAKWCXJP-UHFFFAOYSA-N (4-chlorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=C(Cl)C=C1 AVNCAFPAKWCXJP-UHFFFAOYSA-N 0.000 description 1
- 125000004743 1-methylethoxycarbonyl group Chemical group CC(C)OC(=O)* 0.000 description 1
- LYBKTSWEHSRGKC-UHFFFAOYSA-N 2-bromoethyl-[3-(trifluoromethyl)phenyl]carbamic acid Chemical compound BrCCN(C(O)=O)C1=CC(=CC=C1)C(F)(F)F LYBKTSWEHSRGKC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BOKZZMKECYYWNM-UHFFFAOYSA-N CC1=CC=C(C=C1)N(CCBr)C(O)=O Chemical compound CC1=CC=C(C=C1)N(CCBr)C(O)=O BOKZZMKECYYWNM-UHFFFAOYSA-N 0.000 description 1
- 101100504320 Caenorhabditis elegans mcp-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 108010088874 Cullin 1 Proteins 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000486030 Simnia avena Species 0.000 description 1
- 241001476982 Streptomyces ipomoeae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- LKDBNSDHTCEZLY-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] n-(2-bromoethyl)-n-(2-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)N(CCBr)C=2C(=CC=CC=2)C)=C1 LKDBNSDHTCEZLY-UHFFFAOYSA-N 0.000 description 1
- DNWKZHXTBHCPFN-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] carbonochloridate Chemical compound COC(=O)NC1=CC=CC(OC(Cl)=O)=C1 DNWKZHXTBHCPFN-UHFFFAOYSA-N 0.000 description 1
- PGJMZWORYANMIW-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-(2-bromoethyl)-n-(3-chlorophenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(OC(=O)N(CCBr)C=2C=C(Cl)C=CC=2)=C1 PGJMZWORYANMIW-UHFFFAOYSA-N 0.000 description 1
- SSQUFIKXGKCKJE-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-(2-chloroethyl)-n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC(OC(=O)N(CCCl)C=2C=CC=CC=2)=C1 SSQUFIKXGKCKJE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- CEWKHVQYIATTIC-UHFFFAOYSA-N butyl(phenyl)carbamic acid Chemical compound CCCCN(C(O)=O)C1=CC=CC=C1 CEWKHVQYIATTIC-UHFFFAOYSA-N 0.000 description 1
- PETIIFSZJUYRRP-UHFFFAOYSA-N butyl-(4-methylphenyl)carbamic acid Chemical compound C(CCC)N(C(O)=O)C1=CC=C(C=C1)C PETIIFSZJUYRRP-UHFFFAOYSA-N 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-N butylcarbamic acid Chemical compound CCCCNC(O)=O ZZHGIUCYKGFIPV-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- HYHWDGZUQOWSCT-UHFFFAOYSA-N dibutylcarbamic acid Chemical compound CCCCN(C(O)=O)CCCC HYHWDGZUQOWSCT-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- AAPAVYWERMFERN-UHFFFAOYSA-N ethyl(phenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1 AAPAVYWERMFERN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- UIMCAHUVQVVYPJ-UHFFFAOYSA-N pentyl(phenyl)carbamic acid Chemical compound CCCCCN(C(O)=O)C1=CC=CC=C1 UIMCAHUVQVVYPJ-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752557552 DE2557552C2 (de) | 1975-12-18 | 1975-12-18 | Diurethane und herbizide Mittel, enthaltend diese Verbindungen als Wirkstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44673L IE44673L (en) | 1977-06-18 |
| IE44673B1 true IE44673B1 (en) | 1982-02-24 |
Family
ID=5964983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE273776A IE44673B1 (en) | 1975-12-18 | 1976-12-15 | Herbicidally active diurethanes,process for their manufacture and their use |
Country Status (18)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2650796A1 (de) * | 1976-11-03 | 1978-05-11 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
| DE2819748C2 (de) * | 1978-05-02 | 1986-07-31 | Schering AG, 1000 Berlin und 4709 Bergkamen | N-Äthylcarbanilsäure-(3-methoxycarbonylamino)-phenylester, Verfahren zur Herstellung dieser Verbindung sowie diese enthaltendes selektives herbizides Mittel |
| DE2901658A1 (de) * | 1979-01-15 | 1980-07-24 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| DE2913975A1 (de) * | 1979-04-05 | 1980-10-23 | Schering Ag | N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| CN103191552A (zh) * | 2013-02-12 | 2013-07-10 | 陇东学院 | 网球球拍 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3404975A (en) * | 1964-12-18 | 1968-10-08 | Fmc Corp | m-(carbamoyloxy)-carbanilates as herbicides |
| DE2310648C3 (de) * | 1973-03-01 | 1982-05-06 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende selektive herbizide Mittel |
| DE2413933A1 (de) * | 1974-03-20 | 1975-09-25 | Schering Ag | Diurethane mit selektiver herbizider wirkung |
-
1975
- 1975-12-18 DE DE19752557552 patent/DE2557552C2/de not_active Expired
-
1976
- 1976-09-03 ES ES451210A patent/ES451210A1/es not_active Expired
- 1976-09-17 CS CS605376A patent/CS189033B2/cs unknown
- 1976-09-21 BR BR7606269A patent/BR7606269A/pt unknown
- 1976-10-12 DK DK457776A patent/DK457776A/da not_active Application Discontinuation
- 1976-10-20 LU LU76039A patent/LU76039A1/xx unknown
- 1976-11-10 DD DD19570376A patent/DD126945A5/xx unknown
- 1976-11-24 IL IL50979A patent/IL50979A/xx unknown
- 1976-12-08 SU SU762427098A patent/SU691084A3/ru active
- 1976-12-13 SU SU762427160A patent/SU604457A3/ru active
- 1976-12-13 GB GB51914/76A patent/GB1572542A/en not_active Expired
- 1976-12-15 IE IE273776A patent/IE44673B1/en unknown
- 1976-12-17 ZA ZA767508A patent/ZA767508B/xx unknown
- 1976-12-17 BE BE173413A patent/BE849571A/xx not_active IP Right Cessation
- 1976-12-17 AU AU20670/76A patent/AU507844B2/en not_active Expired
- 1976-12-17 IT IT3052776A patent/IT1065794B/it active
- 1976-12-17 JP JP15187276A patent/JPS5277033A/ja active Granted
- 1976-12-17 NL NL7614034A patent/NL7614034A/xx not_active Application Discontinuation
- 1976-12-20 FR FR7638305A patent/FR2335496A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5277033A (en) | 1977-06-29 |
| LU76039A1 (enrdf_load_stackoverflow) | 1977-05-16 |
| AU507844B2 (en) | 1980-02-28 |
| BE849571A (fr) | 1977-06-17 |
| IL50979A0 (en) | 1977-01-31 |
| ES451210A1 (es) | 1977-09-16 |
| NL7614034A (nl) | 1977-06-21 |
| CS189033B2 (en) | 1979-03-30 |
| ZA767508B (en) | 1977-11-30 |
| FR2335496B1 (enrdf_load_stackoverflow) | 1982-05-21 |
| DD126945A5 (enrdf_load_stackoverflow) | 1977-08-24 |
| SU604457A3 (ru) | 1978-04-25 |
| DE2557552A1 (de) | 1977-06-30 |
| IL50979A (en) | 1981-05-20 |
| BR7606269A (pt) | 1978-04-04 |
| AU2067076A (en) | 1978-06-22 |
| SU691084A3 (ru) | 1979-10-05 |
| DE2557552C2 (de) | 1984-12-20 |
| DK457776A (da) | 1977-06-19 |
| JPS5639308B2 (enrdf_load_stackoverflow) | 1981-09-11 |
| IT1065794B (it) | 1985-03-04 |
| GB1572542A (en) | 1980-07-30 |
| FR2335496A1 (fr) | 1977-07-15 |
| IE44673L (en) | 1977-06-18 |
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