FI64362C - 2-(dimetylkarbamoylimino)-1,3,4-tiadiazolin-3-id-salter foer anvaendning i herbicider - Google Patents
2-(dimetylkarbamoylimino)-1,3,4-tiadiazolin-3-id-salter foer anvaendning i herbicider Download PDFInfo
- Publication number
- FI64362C FI64362C FI771323A FI771323A FI64362C FI 64362 C FI64362 C FI 64362C FI 771323 A FI771323 A FI 771323A FI 771323 A FI771323 A FI 771323A FI 64362 C FI64362 C FI 64362C
- Authority
- FI
- Finland
- Prior art keywords
- substituted
- compounds
- thiadiazolin
- ooo
- salts
- Prior art date
Links
- -1 DIMETHYLCARBAMOYLIMINO Chemical class 0.000 title description 28
- 239000004009 herbicide Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 244000042664 Matricaria chamomilla Species 0.000 description 8
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 8
- 241000209072 Sorghum Species 0.000 description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 241001101998 Galium Species 0.000 description 7
- 241000520028 Lamium Species 0.000 description 7
- 235000017945 Matricaria Nutrition 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000132570 Centaurea Species 0.000 description 6
- 241000723353 Chrysanthemum Species 0.000 description 6
- 235000007516 Chrysanthemum Nutrition 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 240000006694 Stellaria media Species 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000743985 Alopecurus Species 0.000 description 4
- 241000219318 Amaranthus Species 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000192043 Echinochloa Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000205407 Polygonum Species 0.000 description 4
- 241000780602 Senecio Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- 159000000002 lithium salts Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 239000003995 emulsifying agent 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
- 239000000203 mixture Substances 0.000 description 2
- 210000002741 palatine tonsil Anatomy 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- IHVVVNGPIPAMRE-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=NN=C(C(C)(C)C)S1 IHVVVNGPIPAMRE-UHFFFAOYSA-N 0.000 description 1
- RVDUJCGAAPQDBO-UHFFFAOYSA-N 3-hydroxythiophene-2-carboxylic acid Chemical class OC(=O)C=1SC=CC=1O RVDUJCGAAPQDBO-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- PTTVQUAMLAYTAP-UHFFFAOYSA-N CN(C(=O)N1C(SC(=N1)CC)NC(N(C)C)=O)C Chemical compound CN(C(=O)N1C(SC(=N1)CC)NC(N(C)C)=O)C PTTVQUAMLAYTAP-UHFFFAOYSA-N 0.000 description 1
- BPVFBIYHQCSPNN-UHFFFAOYSA-N CN(C(=O)N1C(SC=N1)NC(N(C)C)=O)C Chemical class CN(C(=O)N1C(SC=N1)NC(N(C)C)=O)C BPVFBIYHQCSPNN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 101100417900 Clostridium acetobutylicum (strain ATCC 824 / DSM 792 / JCM 1419 / LMG 5710 / VKM B-1787) rbr3A gene Proteins 0.000 description 1
- 229910017489 Cu I Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 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 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PZYAYFPGUMSVJW-UHFFFAOYSA-N SSSSSSS Chemical compound SSSSSSS PZYAYFPGUMSVJW-UHFFFAOYSA-N 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000012480 Solanum sp Nutrition 0.000 description 1
- 235000019892 Stellar Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000003118 aryl group Chemical group 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
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FISPASSVCDRERW-OEMCRPOKSA-L heme o Chemical compound C\1=C(\N2[Fe]N34)C(C(O)CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)\C2=C\C(C(=C/2CCC(O)=O)C)=N\C\2=C/C3=C(CCC(O)=O)C(C)=C4\C=C/2C(C=C)=C(C)C/1=N\2 FISPASSVCDRERW-OEMCRPOKSA-L 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000013558 reference substance 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762623657 DE2623657A1 (de) | 1976-05-24 | 1976-05-24 | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-salze, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| DE2623657 | 1976-05-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771323A7 FI771323A7 (enrdf_load_stackoverflow) | 1977-11-25 |
| FI64362B FI64362B (fi) | 1983-07-29 |
| FI64362C true FI64362C (fi) | 1983-11-10 |
Family
ID=5979098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771323A FI64362C (fi) | 1976-05-24 | 1977-04-26 | 2-(dimetylkarbamoylimino)-1,3,4-tiadiazolin-3-id-salter foer anvaendning i herbicider |
Country Status (36)
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| US3565901A (en) * | 1969-01-29 | 1971-02-23 | Air Prod & Chem | Certain salts of 1,3,4-thiadiazol-2-ylureas |
| CH554886A (fr) * | 1970-01-15 | 1974-10-15 | Air Prod & Chem | Procede de preparation de thiadiazoles. |
| CH556862A (en) * | 1970-01-15 | 1974-12-13 | Air Prod & Chem | 1-(1,3,4-Thiadiazol-2-yl)-urea derivs as herbicides - and fungicides, prepd. from 2-amino-1,3,4-thiadiazoles |
| CH570391A5 (en) * | 1970-01-15 | 1975-12-15 | Air Prod & Chem | 1,3,4-Thiadiazole herbicides and fungicides - prepd. by reaction of carbamoyl chlorides with alkali metal derivs. of 2-amino-1,3,4-thiadiazoles |
| US3803164A (en) * | 1972-05-22 | 1974-04-09 | Lilly Co Eli | Simplified one vessel preparation of 1-(5-alkyl-1,3,4-thiadiazol-2-yl)-1,3-dialkyl-ureas with azeotropic drying |
| JPS5235672B2 (enrdf_load_stackoverflow) * | 1972-05-22 | 1977-09-10 | ||
| JPS4929189A (enrdf_load_stackoverflow) * | 1972-07-07 | 1974-03-15 | ||
| FR2237894A1 (en) * | 1973-06-29 | 1975-02-14 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| JPS5220533A (en) * | 1975-08-05 | 1977-02-16 | Nippon Soken Inc | Collision detection apparatus |
-
1976
- 1976-05-24 DE DE19762623657 patent/DE2623657A1/de not_active Withdrawn
-
1977
- 1977-03-29 DK DK137577A patent/DK143228C/da not_active IP Right Cessation
- 1977-03-30 YU YU839/77A patent/YU39588B/xx unknown
- 1977-04-08 SU SU772468119A patent/SU701538A3/ru active
- 1977-04-18 NL NL7704219A patent/NL7704219A/xx not_active Application Discontinuation
- 1977-04-22 ES ES458100A patent/ES458100A1/es not_active Expired
- 1977-04-22 BR BR7702545A patent/BR7702545A/pt unknown
- 1977-04-26 FI FI771323A patent/FI64362C/fi not_active IP Right Cessation
- 1977-04-26 BG BG036126A patent/BG27900A3/xx unknown
- 1977-04-27 IN IN609/CAL/77A patent/IN155913B/en unknown
- 1977-05-04 MX MX775713U patent/MX4627E/es unknown
- 1977-05-05 IL IL52034A patent/IL52034A/xx unknown
- 1977-05-09 GB GB19295/77A patent/GB1582571A/en not_active Expired
- 1977-05-10 NZ NZ184056A patent/NZ184056A/xx unknown
- 1977-05-13 IE IE989/77A patent/IE45196B1/en unknown
- 1977-05-17 TR TR20262A patent/TR20262A/xx unknown
- 1977-05-19 PH PH19788A patent/PH14097A/en unknown
- 1977-05-19 CS CS773305A patent/CS195333B2/cs unknown
- 1977-05-20 DD DD7700199045A patent/DD129853A5/xx unknown
- 1977-05-20 CA CA278,903A patent/CA1090350A/en not_active Expired
- 1977-05-20 RO RO7790421A patent/RO72225A/ro unknown
- 1977-05-20 CH CH627377A patent/CH630234A5/de not_active IP Right Cessation
- 1977-05-21 PL PL1977198291A patent/PL102738B1/pl unknown
- 1977-05-23 HU HU77SCHE607A patent/HU180092B/hu unknown
- 1977-05-23 FR FR7715683A patent/FR2352809A1/fr active Granted
- 1977-05-23 IT IT23863/77A patent/IT1080397B/it active
- 1977-05-23 LU LU77391A patent/LU77391A1/xx unknown
- 1977-05-23 SE SE7705982A patent/SE422792B/xx unknown
- 1977-05-23 AU AU25418/77A patent/AU512025B2/en not_active Expired
- 1977-05-23 PT PT66587A patent/PT66587B/pt unknown
- 1977-05-23 GR GR53537A patent/GR72091B/el unknown
- 1977-05-23 EG EG311/77A patent/EG12841A/xx active
- 1977-05-24 BE BE177847A patent/BE854971A/xx not_active IP Right Cessation
- 1977-05-24 ZA ZA00773127A patent/ZA773127B/xx unknown
- 1977-05-24 AT AT370077A patent/AT355368B/de not_active IP Right Cessation
- 1977-05-24 JP JP6038277A patent/JPS52144671A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI64355C (fi) | Acetanilider med herbicid verkan | |
| US4795486A (en) | Aminopyrazinones and aminotriazinones | |
| EP0532146A1 (en) | Herbicidal substituted bicyclic triazoles | |
| JPH0228159A (ja) | 複素環式２―アルコキシフエノキシスルホニル尿素類、それらの製造方法およびそれらを含有する除草剤 | |
| CH649081A5 (de) | Triaza-verbindungen. | |
| DK165690B (da) | Substituerede 2,4-diamino-5-cyano-pyrimidiner og syreadditionssalte deraf, fremgangsmaade til deres fremstilling, middel indeholdende disse forbindelser samt deres anvendelse til topisk bekaempelse af skadeorganismer paa dyr og planter | |
| CA2073446C (en) | Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use | |
| TW492841B (en) | Herbicidal composition and method of weed control | |
| HU212127B (en) | Herbicidal compositions containing sulfonylurea derivative as active ingredient against graminaceous weeds in field of small grain cereals and use of them | |
| FI64362C (fi) | 2-(dimetylkarbamoylimino)-1,3,4-tiadiazolin-3-id-salter foer anvaendning i herbicider | |
| US4721522A (en) | 1H-Imidazo [1',2':1,2]pyrrolo[3,4-b]pyridines and their use as herbicidal agents | |
| HUT55378A (en) | Process for producing 2-azolylnicotinate derivatives and herbicidal compositions comprising such compounds | |
| NZ232980A (en) | (((1,3,5-triazin-2-yl)aminocarbonyl)aminosulphonyl) benzoic esters and herbicidal compositions | |
| FI62305C (fi) | Pentaaza-tetracyklo-dodekadiendrivat anvaendbara foer reglering av vaexters tillvaext | |
| US4789394A (en) | Annularly-linked triazole compounds | |
| EP0285565B1 (de) | 2-Mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel | |
| US4824471A (en) | Heterocyclylalkyl esters of 2-imidazolinonenicotinic acids | |
| US5131946A (en) | Anilino iminoazoles and iminoazines, process for their preparation and their uses | |
| US4946492A (en) | 5-(pyrazol-1-yl)-benzoic acid thiol esters, plant growth regulating compositions and use | |
| HU205540B (en) | Growth regulating and herbicidal compositions comprising heterocyclic substituted phenoxysulfonylurea as active ingredient and process for producing such compounds and for using such compositions | |
| CA1192912A (en) | N-sulphenylated benzylsulphonamides, a process and their use as microbicides | |
| KR920001304B1 (ko) | 에폭사이드 제초제 | |
| DK165934B (da) | Herbicidt middel samt dets anvendelse til bekaempelse af uoensket plantevaekst i nytteplantekulturer og fremgangsmaade til bekaempelse af ukrudt | |
| JPH02229172A (ja) | Ｎ―（フェニル）―テトラヒドロインダゾール誘導体及び該誘導体を含有する除草剤 | |
| CS236871B2 (en) | Herbicide agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SCHERING AG |