CS197327B2 - Herbicide means and method of making the active agent thereof - Google Patents
Herbicide means and method of making the active agent thereof Download PDFInfo
- Publication number
- CS197327B2 CS197327B2 CS784789A CS478978A CS197327B2 CS 197327 B2 CS197327 B2 CS 197327B2 CS 784789 A CS784789 A CS 784789A CS 478978 A CS478978 A CS 478978A CS 197327 B2 CS197327 B2 CS 197327B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- ester
- acid
- methylcarbanilic
- carbanilic
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 5
- 239000013543 active substance Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000004009 herbicide Substances 0.000 title description 2
- 150000001875 compounds Chemical group 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052717 sulfur Chemical group 0.000 claims abstract description 3
- -1 methoxyethyl Chemical group 0.000 claims description 98
- 239000002253 acid Substances 0.000 claims description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 13
- 229920000742 Cotton Polymers 0.000 abstract description 3
- 244000000626 Daucus carota Species 0.000 abstract description 3
- 235000002767 Daucus carota Nutrition 0.000 abstract description 3
- 240000007594 Oryza sativa Species 0.000 abstract description 3
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 3
- 244000061456 Solanum tuberosum Species 0.000 abstract description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
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- 244000299507 Gossypium hirsutum Species 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
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- 235000012015 potatoes Nutrition 0.000 abstract description 2
- 239000011593 sulfur Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004983 dialkoxyalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 83
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 13
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- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 7
- 235000010460 mustard Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 6
- PYJOSHDBCVEHSA-UHFFFAOYSA-N 2,2-dimethoxyethyl(phenyl)carbamic acid Chemical compound COC(OC)CN(C(O)=O)C1=CC=CC=C1 PYJOSHDBCVEHSA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZFZPIYLWLOTMSI-UHFFFAOYSA-N 2,2-dimethoxyethyl-(3-methylphenyl)carbamic acid Chemical compound COC(CN(C(O)=O)C1=CC(=CC=C1)C)OC ZFZPIYLWLOTMSI-UHFFFAOYSA-N 0.000 description 4
- RLCNIFASNGVYMF-UHFFFAOYSA-N 2-ethoxyethyl(phenyl)carbamic acid Chemical compound CCOCCN(C(O)=O)C1=CC=CC=C1 RLCNIFASNGVYMF-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
- MICAYBZEKACXBX-UHFFFAOYSA-N 2,2-dimethoxyethyl-(4-methylphenyl)carbamic acid Chemical compound COC(CN(C(O)=O)C1=CC=C(C=C1)C)OC MICAYBZEKACXBX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KZFJVVPFVUZBJL-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-(2-methoxyethyl)-N-(3-methylphenyl)carbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)C)CCOC)=O)C KZFJVVPFVUZBJL-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HNAXBZUMENBWSX-UHFFFAOYSA-N (3-methylphenyl)carbamic acid Chemical compound CC1=CC=CC(NC(O)=O)=C1 HNAXBZUMENBWSX-UHFFFAOYSA-N 0.000 description 2
- LLROXYDGYRPLFN-UHFFFAOYSA-N 2,2-diethoxyethyl(phenyl)carbamic acid Chemical compound C(C)OC(CN(C(O)=O)C1=CC=CC=C1)OCC LLROXYDGYRPLFN-UHFFFAOYSA-N 0.000 description 2
- DRQLZONZZZAUPR-UHFFFAOYSA-N 2-butoxyethyl(phenyl)carbamic acid Chemical compound C(CCC)OCCN(C(O)=O)C1=CC=CC=C1 DRQLZONZZZAUPR-UHFFFAOYSA-N 0.000 description 2
- ZLFMEZDAVMJTQX-UHFFFAOYSA-N 2-butoxyethyl-(3-methylphenyl)carbamic acid Chemical compound C(CCC)OCCN(C(O)=O)C1=CC(=CC=C1)C ZLFMEZDAVMJTQX-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- KLOCQEAEAAXJPF-UHFFFAOYSA-N 2-ethoxyethyl-(3-methylphenyl)carbamic acid Chemical compound C(C)OCCN(C(O)=O)C1=CC(=CC=C1)C KLOCQEAEAAXJPF-UHFFFAOYSA-N 0.000 description 2
- JKTUWYNLJVOQIV-UHFFFAOYSA-N 2-ethoxyethyl-(4-methylphenyl)carbamic acid Chemical compound C(C)OCCN(C(O)=O)C1=CC=C(C=C1)C JKTUWYNLJVOQIV-UHFFFAOYSA-N 0.000 description 2
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- RWGUGNOAHOFXBV-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(3-methylphenyl)-N-(2-propoxyethyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)C)CCOCCC)=O RWGUGNOAHOFXBV-UHFFFAOYSA-N 0.000 description 1
- LJCVIOUSRZIIRF-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(4-methylphenyl)-N-(2-propoxyethyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)C)CCOCCC)=O LJCVIOUSRZIIRF-UHFFFAOYSA-N 0.000 description 1
- GUUNZWXDMOKFEY-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-phenyl-N-(2-propoxyethyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CCOCCC)=O GUUNZWXDMOKFEY-UHFFFAOYSA-N 0.000 description 1
- RMLROPAOXLMMOK-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2,2-diethoxyethyl)-N-phenylcarbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC(OCC)OCC)=O RMLROPAOXLMMOK-UHFFFAOYSA-N 0.000 description 1
- BBSFTVACHSZPRM-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2,2-dimethoxyethyl)-N-(4-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)C)CC(OC)OC)=O BBSFTVACHSZPRM-UHFFFAOYSA-N 0.000 description 1
- LBCYBDXFDLYHLU-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2,2-dimethoxyethyl)-N-phenylcarbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC(OC)OC)=O LBCYBDXFDLYHLU-UHFFFAOYSA-N 0.000 description 1
- YICHVUSZVXAHFH-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-butoxyethyl)-N-(4-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)C)CCOCCCC)=O YICHVUSZVXAHFH-UHFFFAOYSA-N 0.000 description 1
- TYSKSAZXMXVKAZ-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-ethoxyethyl)-N-(2-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)C)CCOCC)=O TYSKSAZXMXVKAZ-UHFFFAOYSA-N 0.000 description 1
- ZNBJTCOSBRDHSP-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-ethoxyethyl)-N-(4-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)C)CCOCC)=O ZNBJTCOSBRDHSP-UHFFFAOYSA-N 0.000 description 1
- IMPNGWUBOLIZPM-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-ethoxyethyl)-N-phenylcarbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CCOCC)=O IMPNGWUBOLIZPM-UHFFFAOYSA-N 0.000 description 1
- KHKQGXDPZMBBCC-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-methoxyethyl)-N-(2-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)C)CCOC)=O KHKQGXDPZMBBCC-UHFFFAOYSA-N 0.000 description 1
- OJHLXHVVLUZZDP-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-methoxyethyl)-N-(3-methoxyphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)OC)CCOC)=O OJHLXHVVLUZZDP-UHFFFAOYSA-N 0.000 description 1
- CZCZNORGJCPKOM-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-methoxyethyl)-N-(3-methylphenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)C)CCOC)=O CZCZNORGJCPKOM-UHFFFAOYSA-N 0.000 description 1
- XTBBEAFAJCXUAC-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(3-methylphenyl)-N-(2-propoxyethyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)C)CCOCCC)=O XTBBEAFAJCXUAC-UHFFFAOYSA-N 0.000 description 1
- STGRLTSVECDUET-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-phenyl-N-(2-propoxyethyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CCOCCC)=O STGRLTSVECDUET-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000006629 isopropoxycarbonylamino group Chemical group 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772732848 DE2732848A1 (de) | 1977-07-18 | 1977-07-18 | Diurethane, herbizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197327B2 true CS197327B2 (en) | 1980-04-30 |
Family
ID=6014434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784789A CS197327B2 (en) | 1977-07-18 | 1978-07-18 | Herbicide means and method of making the active agent thereof |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4441915A (de) |
| JP (1) | JPS5422340A (de) |
| AU (1) | AU519399B2 (de) |
| BE (1) | BE869074A (de) |
| CA (1) | CA1103268A (de) |
| CH (1) | CH637372A5 (de) |
| CS (1) | CS197327B2 (de) |
| DD (1) | DD137822A5 (de) |
| DE (1) | DE2732848A1 (de) |
| DK (1) | DK320778A (de) |
| ES (1) | ES471736A1 (de) |
| FR (1) | FR2398053A1 (de) |
| GB (1) | GB2002356B (de) |
| GR (1) | GR73026B (de) |
| HU (1) | HU180531B (de) |
| IE (1) | IE47234B1 (de) |
| IL (1) | IL55156A (de) |
| IT (1) | IT1097530B (de) |
| LU (1) | LU79980A1 (de) |
| NL (1) | NL7807482A (de) |
| PL (1) | PL111138B1 (de) |
| PT (1) | PT68309A (de) |
| SU (2) | SU717990A3 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE50640B1 (en) * | 1980-04-28 | 1986-05-28 | Stauffer Chemical Co | Synergistic herbicidal compositions and use thereof |
| GR78909B (de) * | 1982-08-13 | 1984-10-02 | Sipcam Spa | |
| US6150328A (en) * | 1986-07-01 | 2000-11-21 | Genetics Institute, Inc. | BMP products |
| US20080139474A1 (en) * | 1991-11-04 | 2008-06-12 | David Israel | Recombinant bone morphogenetic protein heterodimers, compositions and methods of use |
| EP0612348B1 (de) | 1991-11-04 | 2003-04-23 | Genetics Institute, LLC | Rekombinante knochenmorphogenetische protein heterodimere, zusammensetzungen und verfahren zur verwendung |
| US6291206B1 (en) * | 1993-09-17 | 2001-09-18 | Genetics Institute, Inc. | BMP receptor proteins |
| EP0733109B9 (de) | 1993-12-07 | 2006-07-05 | Genetics Institute, LLC | Bmp-12, bmp-13 und diese enthaltende sehne-induzierende zusammensetzungen |
| US6727224B1 (en) * | 1999-02-01 | 2004-04-27 | Genetics Institute, Llc. | Methods and compositions for healing and repair of articular cartilage |
| US7189392B1 (en) | 1999-10-15 | 2007-03-13 | Genetics Institute, Llc | Injectable carrier formulations of hyaluronic acid derivatives for delivery of osteogenic proteins |
| US20030082233A1 (en) * | 2000-12-01 | 2003-05-01 | Lyons Karen M. | Method and composition for modulating bone growth |
| ATE393573T1 (de) * | 2001-06-01 | 2008-05-15 | Wyeth Corp | Zusammensetzungen für die systemische verabreichung von sequenzen, die für knochenmorphogenese-proteinen kodieren |
| TWI267378B (en) * | 2001-06-08 | 2006-12-01 | Wyeth Corp | Calcium phosphate delivery vehicles for osteoinductive proteins |
| CN1665525A (zh) * | 2002-05-17 | 2005-09-07 | 惠氏公司 | 用于递送骨生成蛋白质的可注入固体透明质酸载体 |
| ATE357244T1 (de) * | 2003-09-12 | 2007-04-15 | Wyeth Corp | Injizierbare feste calciumphosphat-stäbe zur abgabe von osteogenen proteinen |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133808A (en) * | 1959-03-16 | 1964-05-19 | Monsanto Chemicals | Herbicide composition |
| US3404975A (en) * | 1964-12-18 | 1968-10-08 | Fmc Corp | m-(carbamoyloxy)-carbanilates as herbicides |
| DE1567151C3 (de) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel |
| US3551477A (en) * | 1966-07-06 | 1970-12-29 | Basf Ag | Novel biscarbamates |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| US3865867A (en) * | 1967-06-19 | 1975-02-11 | Monsanto Co | Meta-bifunctional benzenes |
| DE2108975C3 (de) * | 1971-02-16 | 1979-12-20 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-Acyl-Diurethane sowie diese enthaltendes herbizides Mittel |
| EG10699A (en) * | 1971-06-23 | 1976-07-31 | Bayer Ag | Novel n.carbamic aryl acid esters method for preparation and their use for controlling plant growth |
| US4022611A (en) * | 1972-06-06 | 1977-05-10 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US3997325A (en) * | 1973-05-24 | 1976-12-14 | American Cyanamid Company | (Alkynyloxy)alkyl and (alkenyloxy)alkyl carbamates and their use as herbicides |
| US3976470A (en) * | 1975-07-23 | 1976-08-24 | Stauffer Chemical Company | Diphenyl ether amides |
-
1977
- 1977-07-18 DE DE19772732848 patent/DE2732848A1/de not_active Withdrawn
-
1978
- 1978-07-03 SU SU782632100A patent/SU717990A3/ru active
- 1978-07-11 NL NL7807482A patent/NL7807482A/xx not_active Application Discontinuation
- 1978-07-12 SU SU782633658A patent/SU858561A3/ru active
- 1978-07-12 CA CA307,243A patent/CA1103268A/en not_active Expired
- 1978-07-14 ES ES471736A patent/ES471736A1/es not_active Expired
- 1978-07-14 LU LU79980A patent/LU79980A1/xx unknown
- 1978-07-14 CH CH766978A patent/CH637372A5/de not_active IP Right Cessation
- 1978-07-14 GR GR56776A patent/GR73026B/el unknown
- 1978-07-14 DD DD78206729A patent/DD137822A5/de unknown
- 1978-07-15 PL PL1978208435A patent/PL111138B1/pl unknown
- 1978-07-17 GB GB7830049A patent/GB2002356B/en not_active Expired
- 1978-07-17 IL IL55156A patent/IL55156A/xx unknown
- 1978-07-17 FR FR7821127A patent/FR2398053A1/fr active Granted
- 1978-07-17 IT IT25741/78A patent/IT1097530B/it active
- 1978-07-17 IE IE1440/78A patent/IE47234B1/en unknown
- 1978-07-17 HU HU78SCHE652A patent/HU180531B/hu unknown
- 1978-07-17 JP JP8621978A patent/JPS5422340A/ja active Pending
- 1978-07-17 PT PT68309A patent/PT68309A/de unknown
- 1978-07-18 AU AU38104/78A patent/AU519399B2/en not_active Expired
- 1978-07-18 DK DK320778A patent/DK320778A/da not_active Application Discontinuation
- 1978-07-18 BE BE189340A patent/BE869074A/xx not_active IP Right Cessation
- 1978-07-18 CS CS784789A patent/CS197327B2/cs unknown
-
1981
- 1981-07-15 US US06/283,661 patent/US4441915A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT1097530B (it) | 1985-08-31 |
| FR2398053A1 (fr) | 1979-02-16 |
| IT7825741A0 (it) | 1978-07-17 |
| AU3810478A (en) | 1980-01-24 |
| BE869074A (fr) | 1979-01-18 |
| ES471736A1 (es) | 1979-02-01 |
| DK320778A (da) | 1979-01-19 |
| US4441915A (en) | 1984-04-10 |
| CH637372A5 (de) | 1983-07-29 |
| IL55156A (en) | 1982-11-30 |
| AU519399B2 (en) | 1981-12-03 |
| IL55156A0 (en) | 1978-09-29 |
| FR2398053B1 (de) | 1982-11-19 |
| PL208435A1 (pl) | 1979-03-26 |
| DE2732848A1 (de) | 1979-02-08 |
| PT68309A (de) | 1978-08-01 |
| GB2002356A (en) | 1979-02-21 |
| JPS5422340A (en) | 1979-02-20 |
| SU858561A3 (ru) | 1981-08-23 |
| CA1103268A (en) | 1981-06-16 |
| NL7807482A (nl) | 1979-01-22 |
| IE47234B1 (en) | 1984-01-25 |
| IE781440L (en) | 1979-01-18 |
| LU79980A1 (de) | 1978-12-12 |
| HU180531B (en) | 1983-03-28 |
| SU717990A3 (ru) | 1980-02-25 |
| PL111138B1 (en) | 1980-08-30 |
| GR73026B (de) | 1984-01-25 |
| GB2002356B (en) | 1982-03-03 |
| DD137822A5 (de) | 1979-09-26 |
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