DE2725146A1 - Diurethane und herbizide - Google Patents

Diurethane und herbizide

Info

Publication number: DE2725146A1
Authority: DE; Germany
Prior art keywords: methyl; phenyl; parts; weight; alkyl
Prior art date: 1977-06-03
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19772725146

Other languages

German (de)

English (en)

Inventor

Wolfgang Dipl Chem Dr Rohr

Ulrich Dipl Chem Dr Schirmer

Bruno Wuerzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

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.)

1977-06-03

Filing date

1977-06-03

Publication date

1978-12-14

1977-06-03 Application filed by BASF SE filed Critical BASF SE

1977-06-03 Priority to DE19772725146 priority Critical patent/DE2725146A1/de

1978-05-24 Priority to IL54779A priority patent/IL54779A/xx

1978-05-26 Priority to PT197868091A priority patent/PT68091A/pt

1978-05-29 Priority to CA304,279A priority patent/CA1110264A/en

1978-05-29 Priority to IE1065/78A priority patent/IE46905B1/en

1978-05-29 Priority to AU36576/78A priority patent/AU519196B2/en

1978-05-30 Priority to TR20048A priority patent/TR20048A/xx

1978-05-31 Priority to ES470367A priority patent/ES470367A1/es

1978-06-01 Priority to SU782619253A priority patent/SU725541A3/ru

1978-06-01 Priority to DD78205730A priority patent/DD135853A5/xx

1978-06-01 Priority to BR787803528A priority patent/BR7803528A/pt

1978-06-01 Priority to CS783577A priority patent/CS196429B2/cs

1978-06-01 Priority to DE7878100050T priority patent/DE2860287D1/de

1978-06-01 Priority to PL1978207278A priority patent/PL106564B1/xx

1978-06-01 Priority to EP78100050A priority patent/EP0000030B1/de

1978-06-02 Priority to FI781762A priority patent/FI781762A7/fi

1978-06-02 Priority to AT403178A priority patent/AT358869B/de

1978-06-02 Priority to YU01325/78A priority patent/YU132578A/xx

1978-06-02 Priority to DK247278A priority patent/DK247278A/da

1978-06-02 Priority to NZ187460A priority patent/NZ187460A/xx

1978-06-02 Priority to NO781931A priority patent/NO781931L/no

1978-06-02 Priority to HU78BA3662A priority patent/HU177551B/hu

1978-06-02 Priority to JP6587678A priority patent/JPS543038A/ja

1978-06-02 Priority to ZA00783163A priority patent/ZA783163B/xx

1978-06-02 Priority to IT49686/78A priority patent/IT1104710B/it

1978-12-14 Publication of DE2725146A1 publication Critical patent/DE2725146A1/de

Status Withdrawn legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title claims description 6
-1 nitro, amino Chemical group 0.000 claims description 182
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
230000002363 herbicidal effect Effects 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
150000001602 bicycloalkyls Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 91
239000000460 chlorine Substances 0.000 description 81
241000196324 Embryophyta Species 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
150000003839 salts Chemical class 0.000 description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
150000001875 compounds Chemical class 0.000 description 23
239000000203 mixture Substances 0.000 description 23
239000004480 active ingredient Substances 0.000 description 18
150000002148 esters Chemical class 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
125000001309 chloro group Chemical group Cl* 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
239000006185 dispersion Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000000034 method Methods 0.000 description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000003944 tolyl group Chemical group 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000002904 solvent Substances 0.000 description 8
244000062793 Sorghum vulgare Species 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
ZNOVDQNFEJCRQZ-UHFFFAOYSA-N 3-propan-2-yl-2$l^{4},1,3-benzothiadiazine 2-oxide Chemical compound C1=CC=CC2=NS(=O)N(C(C)C)C=C21 ZNOVDQNFEJCRQZ-UHFFFAOYSA-N 0.000 description 6
244000105624 Arachis hypogaea Species 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
241000520028 Lamium Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
240000006694 Stellaria media Species 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
239000000047 product Substances 0.000 description 6
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 5
241000335053 Beta vulgaris Species 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
244000068988 Glycine max Species 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 5
MJBPUQUGJNAPAZ-AWEZNQCLSA-N butin Chemical compound C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 5
239000004359 castor oil Substances 0.000 description 5
235000019438 castor oil Nutrition 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 5
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
240000002791 Brassica napus Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000221017 Euphorbiaceae Species 0.000 description 4
240000004658 Medicago sativa Species 0.000 description 4
235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical class CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 4
YSJKYAHYBFJVKV-UHFFFAOYSA-N ethyl n-nitrocarbamate Chemical class CCOC(=O)N[N+]([O-])=O YSJKYAHYBFJVKV-UHFFFAOYSA-N 0.000 description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
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125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
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241000018646 Pinus brutia Species 0.000 description 1
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229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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240000003768 Solanum lycopersicum Species 0.000 description 1
244000061457 Solanum nigrum Species 0.000 description 1
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235000011941 Tilia x europaea Nutrition 0.000 description 1
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240000002913 Trifolium pratense Species 0.000 description 1
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244000105016 Vicia faba var. minor Species 0.000 description 1
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240000004922 Vigna radiata Species 0.000 description 1
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244000042327 Vigna sinensis Species 0.000 description 1
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244000042314 Vigna unguiculata Species 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
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241000607479 Yersinia pestis Species 0.000 description 1
241000209149 Zea Species 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
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229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
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235000013877 carbamide Nutrition 0.000 description 1
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PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
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235000014113 dietary fatty acids Nutrition 0.000 description 1
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239000002270 dispersing agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
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239000010459 dolomite Substances 0.000 description 1
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238000000921 elemental analysis Methods 0.000 description 1
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239000004744 fabric Substances 0.000 description 1
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229930195729 fatty acid Chemical class 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
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235000021331 green beans Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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238000005984 hydrogenation reaction Methods 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
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239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
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235000010981 methylcellulose Nutrition 0.000 description 1
238000003801 milling Methods 0.000 description 1
IKSRCCUOUJJGAU-UHFFFAOYSA-N n-methyl-3-nitroaniline Chemical compound CNC1=CC=CC([N+]([O-])=O)=C1 IKSRCCUOUJJGAU-UHFFFAOYSA-N 0.000 description 1
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150000002825 nitriles Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000011197 perejil Nutrition 0.000 description 1
IXRLLLRWRZSZLT-UHFFFAOYSA-N phenyl n-(3-aminophenyl)carbamate Chemical compound NC1=CC=CC(NC(=O)OC=2C=CC=CC=2)=C1 IXRLLLRWRZSZLT-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L25/00—Assemblies consisting of a plurality of semiconductor or other solid state devices
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Landscapes

Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Environmental Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Microelectronics & Electronic Packaging (AREA)
Physics & Mathematics (AREA)
Computer Hardware Design (AREA)
Power Engineering (AREA)
General Physics & Mathematics (AREA)
Condensed Matter Physics & Semiconductors (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polyurethanes Or Polyureas (AREA)

DE19772725146 1977-06-03 1977-06-03 Diurethane und herbizide Withdrawn DE2725146A1 (de)

Priority Applications (25)

Application Number	Priority Date	Filing Date	Title
DE19772725146 DE2725146A1 (de)	1977-06-03	1977-06-03	Diurethane und herbizide
IL54779A IL54779A (en)	1977-06-03	1978-05-24	Sulfur-containing phenyl diurethanes,their preparation and their use as herbicides
PT197868091A PT68091A (fr)	1977-06-03	1978-05-26	Procede pour la preparation d'une composition herbicid contenant diuretane
CA304,279A CA1110264A (en)	1977-06-03	1978-05-29	Sulfurous diurethanes
IE1065/78A IE46905B1 (en)	1977-06-03	1978-05-29	Sulfurous diurethanes
AU36576/78A AU519196B2 (en)	1977-06-03	1978-05-29	Mono and dithio diurethane herbicides
TR20048A TR20048A (tr)	1977-06-03	1978-05-30	Kuekuert ihtiva eden diueretanlar
ES470367A ES470367A1 (es)	1977-06-03	1978-05-31	Procedimiento para la obtencion de un herbicida conteniendo un diuretano
SU782619253A SU725541A3 (en)	1977-06-03	1978-06-01	Herbicidic agent
DD78205730A DD135853A5 (de)	1977-06-03	1978-06-01	Herbizide mittel
BR787803528A BR7803528A (pt)	1977-06-03	1978-06-01	Mistura herbicida
CS783577A CS196429B2 (en)	1977-06-03	1978-06-01	Herbicide
DE7878100050T DE2860287D1 (en)	1977-06-03	1978-06-01	Diurethanes containing sulphur, process for their preparation and their use as herbicides
PL1978207278A PL106564B1 (pl)	1977-06-03	1978-06-01	Srodek chwastobojczy
EP78100050A EP0000030B1 (de)	1977-06-03	1978-06-01	Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide
FI781762A FI781762A7 (fi)	1977-06-03	1978-06-02	Svavelhaltiga diuretaner
AT403178A AT358869B (de)	1977-06-03	1978-06-02	Herbizid
YU01325/78A YU132578A (en)	1977-06-03	1978-06-02	Process for obtaining sulfur containing diurethanes
DK247278A DK247278A (da)	1977-06-03	1978-06-02	Svovlholdige diurethaner til anvendelse som herbicider
NZ187460A NZ187460A (en)	1977-06-03	1978-06-02	Thio-diurerthanes and herbicides therefrom
NO781931A NO781931L (no)	1977-06-03	1978-06-02	Diuretan med herbicid virkning
HU78BA3662A HU177551B (en)	1977-06-03	1978-06-02	Sulfurian herbicides containing diurethane derivatives
JP6587678A JPS543038A (en)	1977-06-03	1978-06-02	Sulfurrcontaining diurethanes and herbicide containing same
ZA00783163A ZA783163B (en)	1977-06-03	1978-06-02	Sulfurous diurethanes
IT49686/78A IT1104710B (it)	1977-06-03	1978-06-02	Diuretani solforati dotati di attivita'diserbante

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772725146 DE2725146A1 (de)	1977-06-03	1977-06-03	Diurethane und herbizide

Publications (1)

Publication Number	Publication Date
DE2725146A1 true DE2725146A1 (de)	1978-12-14

Family

ID=6010672

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE19772725146 Withdrawn DE2725146A1 (de)	1977-06-03	1977-06-03	Diurethane und herbizide
DE7878100050T Expired DE2860287D1 (en)	1977-06-03	1978-06-01	Diurethanes containing sulphur, process for their preparation and their use as herbicides

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DE7878100050T Expired DE2860287D1 (en)	1977-06-03	1978-06-01	Diurethanes containing sulphur, process for their preparation and their use as herbicides

Country Status (24)

Country	Link
EP (1)	EP0000030B1 (xx)
JP (1)	JPS543038A (xx)
AT (1)	AT358869B (xx)
AU (1)	AU519196B2 (xx)
BR (1)	BR7803528A (xx)
CA (1)	CA1110264A (xx)
CS (1)	CS196429B2 (xx)
DD (1)	DD135853A5 (xx)
DE (2)	DE2725146A1 (xx)
DK (1)	DK247278A (xx)
ES (1)	ES470367A1 (xx)
FI (1)	FI781762A7 (xx)
HU (1)	HU177551B (xx)
IE (1)	IE46905B1 (xx)
IL (1)	IL54779A (xx)
IT (1)	IT1104710B (xx)
NO (1)	NO781931L (xx)
NZ (1)	NZ187460A (xx)
PL (1)	PL106564B1 (xx)
PT (1)	PT68091A (xx)
SU (1)	SU725541A3 (xx)
TR (1)	TR20048A (xx)
YU (1)	YU132578A (xx)
ZA (1)	ZA783163B (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5951205A (ja) *	1982-06-23	1984-03-24	Toyo Soda Mfg Co Ltd	カ−バメ−ト誘導体を含有する除草剤
WO1999035122A1 (de) *	1998-01-09	1999-07-15	Bayer Aktiengesellschaft	Verfahren zur herstellung von n-(3-amino-4-fluor-phenyl)-sulfonsäureamiden, n-(3-amino-4-fluor-phenyl)-carbonsäureamiden und n-(3-amino-4-fluor-phenyl)-carbamaten

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3113449A1 (de) *	1981-04-03	1982-11-11	Hoechst Ag, 6000 Frankfurt	"thiocarbaminsaeureester, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und ihre verwendung"

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1037578B (it) *	1975-04-23	1979-11-20	Snam Progetti	Procedimento per la sintesi di esteri di acidi tiocarbammici
JPS537474A (en) *	1976-07-12	1978-01-23	Tsuneto Yoshii	Process for producing soil conditioner and fertilizers from waste woods of artificial bed log for shiitake* shiitake aseptic timber and other edible or medicinal fungi culture base

1977
- 1977-06-03 DE DE19772725146 patent/DE2725146A1/de not_active Withdrawn
1978
- 1978-05-24 IL IL54779A patent/IL54779A/xx unknown
- 1978-05-26 PT PT197868091A patent/PT68091A/pt unknown
- 1978-05-29 CA CA304,279A patent/CA1110264A/en not_active Expired
- 1978-05-29 IE IE1065/78A patent/IE46905B1/en unknown
- 1978-05-29 AU AU36576/78A patent/AU519196B2/en not_active Expired
- 1978-05-30 TR TR20048A patent/TR20048A/xx unknown
- 1978-05-31 ES ES470367A patent/ES470367A1/es not_active Expired
- 1978-06-01 PL PL1978207278A patent/PL106564B1/xx unknown
- 1978-06-01 SU SU782619253A patent/SU725541A3/ru active
- 1978-06-01 DE DE7878100050T patent/DE2860287D1/de not_active Expired
- 1978-06-01 DD DD78205730A patent/DD135853A5/xx unknown
- 1978-06-01 EP EP78100050A patent/EP0000030B1/de not_active Expired
- 1978-06-01 CS CS783577A patent/CS196429B2/cs unknown
- 1978-06-01 BR BR787803528A patent/BR7803528A/pt unknown
- 1978-06-02 FI FI781762A patent/FI781762A7/fi not_active Application Discontinuation
- 1978-06-02 YU YU01325/78A patent/YU132578A/xx unknown
- 1978-06-02 NO NO781931A patent/NO781931L/no unknown
- 1978-06-02 AT AT403178A patent/AT358869B/de not_active IP Right Cessation
- 1978-06-02 JP JP6587678A patent/JPS543038A/ja active Granted
- 1978-06-02 ZA ZA00783163A patent/ZA783163B/xx unknown
- 1978-06-02 NZ NZ187460A patent/NZ187460A/xx unknown
- 1978-06-02 HU HU78BA3662A patent/HU177551B/hu unknown
- 1978-06-02 DK DK247278A patent/DK247278A/da not_active Application Discontinuation
- 1978-06-02 IT IT49686/78A patent/IT1104710B/it active

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5951205A (ja) *	1982-06-23	1984-03-24	Toyo Soda Mfg Co Ltd	カ−バメ−ト誘導体を含有する除草剤
WO1999035122A1 (de) *	1998-01-09	1999-07-15	Bayer Aktiengesellschaft	Verfahren zur herstellung von n-(3-amino-4-fluor-phenyl)-sulfonsäureamiden, n-(3-amino-4-fluor-phenyl)-carbonsäureamiden und n-(3-amino-4-fluor-phenyl)-carbamaten

Also Published As

Publication number	Publication date
HU177551B (en)	1981-11-28
JPS543038A (en)	1979-01-11
ES470367A1 (es)	1979-09-16
ATA403178A (de)	1980-02-15
BR7803528A (pt)	1979-02-20
NO781931L (no)	1978-12-05
EP0000030A1 (de)	1978-12-20
CA1110264A (en)	1981-10-06
PL106564B1 (pl)	1979-12-31
IL54779A (en)	1982-12-31
IL54779A0 (en)	1978-07-31
IT7849686A0 (it)	1978-06-02
PT68091A (fr)	1978-05-31
JPS6151583B2 (xx)	1986-11-10
IT1104710B (it)	1985-10-28
SU725541A1 (ru)	1980-03-30
IE46905B1 (en)	1983-11-02
FI781762A7 (fi)	1978-12-04
AU3657678A (en)	1979-12-06
DE2860287D1 (en)	1981-02-19
EP0000030B1 (de)	1980-12-10
PL207278A1 (pl)	1979-03-26
IE781065L (en)	1978-12-03
DK247278A (da)	1978-12-04
AT358869B (de)	1980-10-10
DD135853A5 (de)	1979-06-06
NZ187460A (en)	1980-11-28
CS196429B2 (en)	1980-03-31
SU725541A3 (en)	1980-03-30
TR20048A (tr)	1980-07-02
YU132578A (en)	1983-01-21
ZA783163B (en)	1979-07-25
AU519196B2 (en)	1981-11-19

Publication	Publication Date	Title
DE2914915A1 (de)	1980-10-30	4h-3,1-benzoxazinderivate
DE4038430A1 (de)	1992-06-04	Herbizide n-((1,3,5-triazin-2-yl)-aminocarbonyl) benzolsulfonamide
DE3305866A1 (de)	1984-08-23	Thiophen-carbonester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
EP0238021A1 (de)	1987-09-23	Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums
DD292917A5 (de)	1991-08-14	Herbizide [[(1,3,5-triazin-2-yl) aminocarbonyl] aminosulfonyl] benzoesaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2703838A1 (de)	1978-08-10	Diurethane
DE3716657A1 (de)	1988-12-01	Herbizide sulfonamide, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des pflanzenwachstums
DE2725146A1 (de)	1978-12-14	Diurethane und herbizide
CH633679A5 (de)	1982-12-31	Herbizide, enthaltend substituierte 2,1,3-benzothiadiazinverbindungen als aktive komponenten.
DE3900472A1 (de)	1990-07-12	Herbizide sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE3601066A1 (de)	1987-07-23	Cyclohexenonderivate, ein verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und das pflanzenwachstum regulierende mittel
EP0107123B1 (de)	1987-07-01	Anilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE2920933A1 (de)	1980-12-04	3-aryl-5-methyl-pyrazol-4-carbonsaeureester enthaltende herbizide
DE3418532A1 (de)	1985-06-13	Chinolinoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
DE2638897C2 (de)	1978-10-26	Diurethane und diese enthaltende Herbizide
DE3830733A1 (de)	1990-03-22	5-(n-3,4,5,6-tetrahydrophthalimido)-zimtsaeurederivate, ihre herstellung und ihre verwendung in herbiziden mitteln
EP0037527A1 (de)	1981-10-14	Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
EP0123727B1 (de)	1986-08-20	Substituierte Harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE2916647A1 (de)	1980-11-06	Parabansaeurederivate
CH634721A5 (de)	1983-02-28	Benzothiadiazinverbindungen enthaltende herbizide.
DE2901626A1 (de)	1980-07-31	N-sulfenylierte diurethane
CH627344A5 (de)	1982-01-15	Herbizid.
DE2844811A1 (de)	1980-09-04	Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel
DE3413755A1 (de)	1985-10-24	Thiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
EP0081207A2 (de)	1983-06-15	Anilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses

Legal Events

Date	Code	Title	Description
1984-08-30	8141	Disposal/no request for examination

DE2725146A1 - Diurethane und herbizide - Google Patents

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Priority Applications (25)

Applications Claiming Priority (1)

Publications (1)

Family

ID=6010672

Family Applications (2)

Family Applications After (1)

Country Status (24)

Cited By (2)

Families Citing this family (1)

Family Cites Families (2)

Cited By (2)

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