NO118324B - - Google Patents
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- Publication number
- NO118324B NO118324B NO159956A NO15995665A NO118324B NO 118324 B NO118324 B NO 118324B NO 159956 A NO159956 A NO 159956A NO 15995665 A NO15995665 A NO 15995665A NO 118324 B NO118324 B NO 118324B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- dimethylureido
- compounds
- methylureido
- herbicidal
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000004009 herbicide Substances 0.000 claims description 9
- SFLPXHOPMULQFJ-UHFFFAOYSA-N [3-(carbamoylamino)phenyl] carbamate Chemical class NC(=O)NC1=CC=CC(OC(N)=O)=C1 SFLPXHOPMULQFJ-UHFFFAOYSA-N 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000005864 Sulphur Chemical group 0.000 claims 1
- -1 N-mono-substituted carbamic acid Chemical class 0.000 description 49
- 230000002363 herbicidal effect Effects 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VTDPFMZYQCJTNK-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl]-methylcarbamic acid Chemical compound CN(C)C(NC1=CC=CC(N(C)C(O)=O)=C1)=O VTDPFMZYQCJTNK-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 240000006240 Linum usitatissimum Species 0.000 description 4
- 235000004431 Linum usitatissimum Nutrition 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 229940018563 3-aminophenol Drugs 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000008415 Lactuca sativa Species 0.000 description 3
- 235000003228 Lactuca sativa Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- IPRCBIWIPMJXIK-UHFFFAOYSA-N (3-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=CC(O)=C1 IPRCBIWIPMJXIK-UHFFFAOYSA-N 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- HQSQPMWCWCOTBH-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(O)=C1 HQSQPMWCWCOTBH-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 244000178993 Brassica juncea Species 0.000 description 2
- 235000011332 Brassica juncea Nutrition 0.000 description 2
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QPXYEFQTSZQARV-UHFFFAOYSA-N (2,4-dichlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(Cl)C=C1Cl QPXYEFQTSZQARV-UHFFFAOYSA-N 0.000 description 1
- QITHMWRZZVHKPY-UHFFFAOYSA-N (4-methylphenyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=C(C)C=C1 QITHMWRZZVHKPY-UHFFFAOYSA-N 0.000 description 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- AUGWUUWYMHUJMW-UHFFFAOYSA-N CC(C)(C)N(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 Chemical compound CC(C)(C)N(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 AUGWUUWYMHUJMW-UHFFFAOYSA-N 0.000 description 1
- XEVOPZLTFJNURU-UHFFFAOYSA-N CCC(C)N(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 Chemical compound CCC(C)N(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 XEVOPZLTFJNURU-UHFFFAOYSA-N 0.000 description 1
- MKHZKTLDTRLHLC-UHFFFAOYSA-N CCCCNC(NC1=CC=CC(N(C)C(O)=O)=C1)=O Chemical compound CCCCNC(NC1=CC=CC(N(C)C(O)=O)=C1)=O MKHZKTLDTRLHLC-UHFFFAOYSA-N 0.000 description 1
- IJZGHRGCGOMWQO-UHFFFAOYSA-N CCN(C(O)=O)C1=CC(NC(N(C)C)=O)=CC=C1 Chemical compound CCN(C(O)=O)C1=CC(NC(N(C)C)=O)=CC=C1 IJZGHRGCGOMWQO-UHFFFAOYSA-N 0.000 description 1
- WYIXOBDSXRXWCZ-UHFFFAOYSA-N CCN(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 Chemical compound CCN(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 WYIXOBDSXRXWCZ-UHFFFAOYSA-N 0.000 description 1
- ZTEWXQZCZJIWBR-UHFFFAOYSA-N CNC(NC1=CC=CC(N(C)C(O)=O)=C1)=O Chemical compound CNC(NC1=CC=CC(N(C)C(O)=O)=C1)=O ZTEWXQZCZJIWBR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000421334 Cerastium fontanum subsp. vulgare Species 0.000 description 1
- 240000006555 Chamaerops humilis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- LDGGJRNNHKPEOF-UHFFFAOYSA-N NC(NC1=CC=CC(NC(O)=O)=C1)=O Chemical compound NC(NC1=CC=CC(NC(O)=O)=C1)=O LDGGJRNNHKPEOF-UHFFFAOYSA-N 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- BFXLQAXFPODEJD-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl] n-(2-methylpropyl)carbamate Chemical compound CC(C)CNC(=O)OC1=CC=CC(NC(=O)N(C)C)=C1 BFXLQAXFPODEJD-UHFFFAOYSA-N 0.000 description 1
- UTTSGXDQLUUBTQ-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl]-(2-methylpropyl)carbamic acid Chemical compound CC(C)CN(C(O)=O)C1=CC(NC(N(C)C)=O)=CC=C1 UTTSGXDQLUUBTQ-UHFFFAOYSA-N 0.000 description 1
- VTDGOWYMEYTFNZ-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl]-propan-2-ylcarbamic acid Chemical compound CC(C)N(C(O)=O)C1=CC(NC(N(C)C)=O)=CC=C1 VTDGOWYMEYTFNZ-UHFFFAOYSA-N 0.000 description 1
- RRRGYJCAGRTYOU-UHFFFAOYSA-N [3-(methylcarbamoylamino)phenyl] n-methylcarbamate Chemical compound CNC(=O)NC1=CC=CC(OC(=O)NC)=C1 RRRGYJCAGRTYOU-UHFFFAOYSA-N 0.000 description 1
- ULMRXPZFCJPJPW-UHFFFAOYSA-N [3-(methylcarbamoylamino)phenyl]-propan-2-ylcarbamic acid Chemical compound CC(C)N(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 ULMRXPZFCJPJPW-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AKTOECZHLOHWKT-UHFFFAOYSA-N boric acid chloric acid Chemical compound B(O)(O)O.Cl(=O)(=O)O AKTOECZHLOHWKT-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BPTCHOSQAFYVPE-UHFFFAOYSA-N ethyl n,n-dipropylcarbamate Chemical compound CCCN(CCC)C(=O)OCC BPTCHOSQAFYVPE-UHFFFAOYSA-N 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- FGBMXRACGFZLOQ-UHFFFAOYSA-N hexyl-[3-(methylcarbamoylamino)phenyl]carbamic acid Chemical compound CCCCCCN(C(O)=O)C1=CC(NC(NC)=O)=CC=C1 FGBMXRACGFZLOQ-UHFFFAOYSA-N 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 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
- 239000011344 liquid material Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- UKRYHACTHFDUQV-UHFFFAOYSA-N methyl-[3-(methylcarbamothioylamino)phenyl]carbamic acid Chemical compound CNC(=S)NC1=CC(=CC=C1)N(C)C(=O)O UKRYHACTHFDUQV-UHFFFAOYSA-N 0.000 description 1
- BPWVAMSYZZOMDL-UHFFFAOYSA-N methyl-[3-[methyl(methylcarbamoyl)amino]phenyl]carbamic acid Chemical compound CNC(=O)N(C)C1=CC=CC(N(C)C(O)=O)=C1 BPWVAMSYZZOMDL-UHFFFAOYSA-N 0.000 description 1
- UXQTZLNCAAZUAZ-UHFFFAOYSA-N methyl-[[3-(methylcarbamoylamino)phenyl]methyl]carbamic acid Chemical compound CNC(NC1=CC=CC(CN(C)C(O)=O)=C1)=O UXQTZLNCAAZUAZ-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- VTUUIKKEQVOLFO-UHFFFAOYSA-N phenyl n,n-di(propan-2-yl)carbamate Chemical compound CC(C)N(C(C)C)C(=O)OC1=CC=CC=C1 VTUUIKKEQVOLFO-UHFFFAOYSA-N 0.000 description 1
- ICGNCPZDLALZBU-UHFFFAOYSA-N phenyl n-butylcarbamate Chemical compound CCCCNC(=O)OC1=CC=CC=C1 ICGNCPZDLALZBU-UHFFFAOYSA-N 0.000 description 1
- GJQFJYAVSJYAOW-UHFFFAOYSA-N phenyl n-cyclohexylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1CCCCC1 GJQFJYAVSJYAOW-UHFFFAOYSA-N 0.000 description 1
- KZMHCQUAMFYNRF-UHFFFAOYSA-N phenyl n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=CC=C1 KZMHCQUAMFYNRF-UHFFFAOYSA-N 0.000 description 1
- OIBVOMMFYSNPKX-UHFFFAOYSA-N phenyl n-prop-2-ynylcarbamate Chemical compound C#CCNC(=O)OC1=CC=CC=C1 OIBVOMMFYSNPKX-UHFFFAOYSA-N 0.000 description 1
- BKVUXKJWTVANMM-UHFFFAOYSA-N phenyl n-tert-butylcarbamate Chemical compound CC(C)(C)NC(=O)OC1=CC=CC=C1 BKVUXKJWTVANMM-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 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
- 230000009528 severe injury Effects 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NVRGZOVGYJMDPQ-UHFFFAOYSA-N tert-butyl-[3-(dimethylcarbamoylamino)phenyl]carbamic acid Chemical compound CN(C)C(=O)NC1=CC=CC(N(C(O)=O)C(C)(C)C)=C1 NVRGZOVGYJMDPQ-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO16171965A NO119121B (ja) | 1964-03-23 | 1965-10-05 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35415364A | 1964-03-23 | 1964-03-23 | |
| US43315765A | 1965-02-16 | 1965-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118324B true NO118324B (ja) | 1969-12-15 |
Family
ID=26998269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159956A NO118324B (ja) | 1964-03-23 | 1965-10-05 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3434822A (ja) |
| AT (1) | AT264198B (ja) |
| BE (1) | BE661399A (ja) |
| BR (1) | BR6568060D0 (ja) |
| CH (1) | CH463870A (ja) |
| DE (1) | DE1518815C3 (ja) |
| DK (1) | DK116698B (ja) |
| ES (1) | ES310664A1 (ja) |
| GB (1) | GB1106064A (ja) |
| IL (1) | IL23190A (ja) |
| NL (1) | NL139522B (ja) |
| NO (1) | NO118324B (ja) |
| SE (1) | SE320656B (ja) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593520C3 (de) * | 1966-09-05 | 1974-07-11 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 3-(Carbamoyloxyphenyl)-harnstoffe bzw. -thioharnstoffe, diese enthaltende Mittel mit selektiver herbizider Wirkung sowie Verfahren zu deren Herstellung |
| CH489999A (de) * | 1966-12-01 | 1970-05-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| US3547979A (en) * | 1968-04-12 | 1970-12-15 | Du Pont | Herbicidal carbamoyloxyphenyl n-alkoxyureas |
| US3670010A (en) * | 1969-05-06 | 1972-06-13 | Stauffer Chemical Co | Trifluoromethyl acylated urea carbamates |
| US3870504A (en) * | 1969-08-13 | 1975-03-11 | Philips Corp | Cycloalkylphenyl ureas as herbicides |
| US4242122A (en) * | 1970-10-02 | 1980-12-30 | Monsanto Company | Herbicidal meta-bifunctional benzenes |
| US4013450A (en) * | 1970-10-02 | 1977-03-22 | Monsanto Company | Herbicidal ureido containing carbanilates |
| US3897493A (en) * | 1971-09-13 | 1975-07-29 | Stauffer Chemical Co | Meta-anilide urea compositions and their utility as herbicides |
| US3885954A (en) * | 1971-12-22 | 1975-05-27 | Scm Corp | Meta-3-alkoxyureidophenyl N-haloalkyl carbamates as herbicides |
| US3885953A (en) * | 1971-12-22 | 1975-05-27 | Scm Corp | Meta-ureidophenyl n-haloalkyl carbamates as herbicides |
| US3927070A (en) * | 1972-05-08 | 1975-12-16 | Karoly Szabo | M-(3,3-disubstituted ureido) phenyl {8 (substituted)methyl{9 {0 carbamates |
| US3954441A (en) * | 1973-03-26 | 1976-05-04 | American Cyanamid Company | (Alkynyloxy)alkyl and (alkenyloxy)alkyl carbamates and their use as herbicides |
| DE2634455A1 (de) * | 1976-07-29 | 1978-02-02 | Schering Ag | Carbaminsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| US4416684A (en) * | 1979-04-02 | 1983-11-22 | Stauffer Chemical Company | Synergistic herbicidal compositions |
| US4381195A (en) * | 1981-04-20 | 1983-04-26 | Stauffer Chemical Company | N-Methylcarbamoyloxy anilides as herbicide extenders |
| US4381196A (en) * | 1981-04-20 | 1983-04-26 | Stauffer Chemical Company | O-(Substituted phenyl) N-methylcarbamates as herbicide extenders |
| EP2052609A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037621A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN113651722A (zh) * | 2021-08-13 | 2021-11-16 | 浙江海昇药业股份有限公司 | 一种1-(3-羟基苯基)-1,3,3-三甲基脲的合成方法、中间体及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL92838C (ja) * | 1949-12-06 | |||
| BE531554A (ja) * | 1953-09-02 | |||
| US3207780A (en) * | 1962-11-15 | 1965-09-21 | Upjohn Co | 1-deoxy-1-guanidino-3-o-carbamoyl-scyllo-inositol and acylates thereof |
-
1965
- 1965-02-16 US US433157A patent/US3434822A/en not_active Expired - Lifetime
- 1965-03-10 GB GB10254/65A patent/GB1106064A/en not_active Expired
- 1965-03-16 SE SE3418/65A patent/SE320656B/xx unknown
- 1965-03-17 ES ES0310664A patent/ES310664A1/es not_active Expired
- 1965-03-19 BE BE661399A patent/BE661399A/xx unknown
- 1965-03-19 CH CH387765A patent/CH463870A/de unknown
- 1965-03-20 DE DE1518815A patent/DE1518815C3/de not_active Expired
- 1965-03-21 IL IL23190A patent/IL23190A/xx unknown
- 1965-03-22 AT AT258165A patent/AT264198B/de active
- 1965-03-23 NL NL656503645A patent/NL139522B/xx not_active IP Right Cessation
- 1965-03-23 DK DK149265AA patent/DK116698B/da unknown
- 1965-03-23 BR BR168060/65A patent/BR6568060D0/pt unknown
- 1965-10-05 NO NO159956A patent/NO118324B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1106064A (en) | 1968-03-13 |
| BE661399A (ja) | 1965-09-20 |
| IL23190A (en) | 1969-05-28 |
| US3434822A (en) | 1969-03-25 |
| DK116698B (da) | 1970-02-02 |
| NL139522B (nl) | 1973-08-15 |
| CH463870A (de) | 1968-10-15 |
| ES310664A1 (es) | 1966-01-01 |
| DE1518815B2 (de) | 1974-02-21 |
| NL6503645A (ja) | 1965-09-24 |
| AT264198B (de) | 1968-08-26 |
| BR6568060D0 (pt) | 1973-07-03 |
| SE320656B (ja) | 1970-02-16 |
| DE1518815A1 (de) | 1969-04-30 |
| DE1518815C3 (de) | 1974-10-17 |
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