NO118324B - - Google Patents

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Publication number: NO118324B
Authority: NO; Norway
Prior art keywords: phenyl; dimethylureido; compounds; methylureido; herbicidal
Prior art date: 1964-03-23

Application number

NO159956A

Other languages

English (en)

Norwegian (no)

Inventor

K Wilson

K Hill

Original Assignee

Fmc Corp

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.)

1964-03-23

Filing date

1965-10-05

Publication date

1969-12-15

1965-10-05 Application filed by Fmc Corp filed Critical Fmc Corp

1965-10-05 Priority to NO16171965A priority Critical patent/NO119121B/no

1969-12-15 Publication of NO118324B publication Critical patent/NO118324B/no

Links

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
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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
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239000000126 substance Substances 0.000 description 3
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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
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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
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240000007049 Juglans regia Species 0.000 description 1
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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
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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
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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
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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
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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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)

NO159956A 1964-03-23 1965-10-05 NO118324B (ja)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 CH CH387765A patent/CH463870A/de unknown
- 1965-03-19 BE BE661399A patent/BE661399A/xx 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
CH463870A (de)	1968-10-15
GB1106064A (en)	1968-03-13
BR6568060D0 (pt)	1973-07-03
NL6503645A (ja)	1965-09-24
DE1518815A1 (de)	1969-04-30
SE320656B (ja)	1970-02-16
BE661399A (ja)	1965-09-20
ES310664A1 (es)	1966-01-01
NL139522B (nl)	1973-08-15
AT264198B (de)	1968-08-26
DE1518815B2 (de)	1974-02-21
IL23190A (en)	1969-05-28
DK116698B (da)	1970-02-02
DE1518815C3 (de)	1974-10-17
US3434822A (en)	1969-03-25

Publication	Publication Date	Title
NO118324B (ja)	1969-12-15
KR900006130B1 (ko)	1990-08-24	살충성 n'-치환-n,n'-디아실히드라진
EP0096003B2 (de)	1994-06-15	Neue Sulfonyl(thio)harnstoffe, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und/oder Wachstumsregulatoren
CA1084529A (en)	1980-08-26	N'- 4-(substituted phenethyloxy)-phenyl -n-methyl-n- methoxyurea
EP0071958B1 (de)	1985-04-10	Heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft
UA57592C2 (uk)	2003-06-16	Гербіцидна композиція
CS242896B2 (en)	1986-05-15	Insecticide and acaricide and method of efficient substances production
EP0103537B1 (de)	1987-07-08	N-Arylsulfonyl-N'-triazolylharnstoffe
DE68908789T2 (de)	1994-04-14	Insectizide N'-substituierte-N-alkylcarbonyl-N'-acylhydrazine und N'-substituierte-N-acyl-N'-alkylcarbonyl hydrazine.
US3639633A (en)	1972-02-01	Substituted o-carbamylhydroxamate pesticides
DD283918A5 (de)	1990-10-31	Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe
NO159956B (no)	1988-11-14	Fjellarmeringsbolt.
HU206592B (en)	1992-12-28	Herbicide and growth controlling compositions containing substituted sulfonyl-diamide derivatives as active components and process for producing the active components
JPH0421672B2 (ja)	1992-04-13
NZ228630A (en)	1991-06-25	Alkyl- and alkenyl- sulphonylurea derivatives, preparation thereof and herbicidal compositions
PL139505B1 (en)	1987-01-31	Pesticide and method of obtaining novel derivatives of benzoilurea
NO161719B (no)	1989-06-12	Fremgangsmaate og anlegg for fremstilling av en fortynnet slurry inneholdende sinkstoev.
US3201220A (en)	1965-08-17	Herbicidal composition and method
UA47429C2 (uk)	2002-07-15	Фунгіцидний засіб
EP0127469A2 (en)	1984-12-05	Antidotes for sulfonylurea herbicides
US3824320A (en)	1974-07-16	Substituted o-carbamylhydroxamate insecticides
US4509974A (en)	1985-04-09	S-n-Butyl-N,N-diisopropyl thiocarbamate as a selective herbicide in cotton
NO119121B (ja)	1970-03-23
JPS5857404B2 (ja)	1983-12-20	除草剤組成物
US4106924A (en)	1978-08-15	Pesticidal compositions