GB2119252A - Use of thiadiazolylimidazolidinones to control aquatic vegetation - Google Patents
Use of thiadiazolylimidazolidinones to control aquatic vegetation Download PDFInfo
- Publication number
- GB2119252A GB2119252A GB08311822A GB8311822A GB2119252A GB 2119252 A GB2119252 A GB 2119252A GB 08311822 A GB08311822 A GB 08311822A GB 8311822 A GB8311822 A GB 8311822A GB 2119252 A GB2119252 A GB 2119252A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- methyl
- hydrogen
- hydroxy
- compound
- Prior art date
- 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- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- -1 dimethylethyl Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 16
- 230000012010 growth Effects 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 230000001276 controlling effect Effects 0.000 claims description 10
- 230000008635 plant growth Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 18
- 239000004009 herbicide Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- VHXDHGALQPVNKI-UHFFFAOYSA-N thiadiazol-4-ylurea Chemical compound NC(=O)NC1=CSN=N1 VHXDHGALQPVNKI-UHFFFAOYSA-N 0.000 description 6
- HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000003630 growth substance Substances 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YDUWBONTVUJVRG-UHFFFAOYSA-N 5-(5-hydroxy-3-methyl-2-oxoimidazolidin-1-yl)-n,n-dimethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound S1C(S(=O)(=O)N(C)C)=NN=C1N1C(=O)N(C)CC1O YDUWBONTVUJVRG-UHFFFAOYSA-N 0.000 description 4
- QSFSCKHIVHWZIP-UHFFFAOYSA-N 5-amino-1,3,4-thiadiazole-2-sulfonyl chloride Chemical compound NC1=NN=C(S(Cl)(=O)=O)S1 QSFSCKHIVHWZIP-UHFFFAOYSA-N 0.000 description 4
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 4
- 241000195493 Cryptophyta Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 240000003826 Eichhornia crassipes Species 0.000 description 4
- 244000052355 Hydrilla verticillata Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000003619 algicide Substances 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- AZVLLJZRAAUHDX-UHFFFAOYSA-N phenyl n-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]carbamate Chemical compound S1C(S(=O)(=O)N(C)C)=NN=C1NC(=O)OC1=CC=CC=C1 AZVLLJZRAAUHDX-UHFFFAOYSA-N 0.000 description 3
- 230000008654 plant damage Effects 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 description 2
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000192707 Synechococcus Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002353 algacidal effect Effects 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- JTPZTKBRUCILQD-UHFFFAOYSA-N 1-methylimidazolidin-2-one Chemical compound CN1CCNC1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 description 1
- VNRIHEIPDHEQIA-UHFFFAOYSA-N 1-sulfonyl-1,3,4-thiadiazole Chemical compound O=S(=O)=S1C=NN=C1 VNRIHEIPDHEQIA-UHFFFAOYSA-N 0.000 description 1
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LQZZHUXKKXACMF-UHFFFAOYSA-N 5-(5-hydroxy-2-oxoimidazolidin-1-yl)-n,n-dimethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound S1C(S(=O)(=O)N(C)C)=NN=C1N1C(=O)NCC1O LQZZHUXKKXACMF-UHFFFAOYSA-N 0.000 description 1
- QHIPKCYRJSMKRT-UHFFFAOYSA-N 5-(5-methoxy-3-methyl-2-oxoimidazolidin-1-yl)-n,n-dimethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound COC1CN(C)C(=O)N1C1=NN=C(S(=O)(=O)N(C)C)S1 QHIPKCYRJSMKRT-UHFFFAOYSA-N 0.000 description 1
- PNVGYZVQSJWYQJ-UHFFFAOYSA-N 5-[5-(dimethylamino)-3-methyl-2-oxoimidazolidin-1-yl]-n,n-dimethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound CN(C)C1CN(C)C(=O)N1C1=NN=C(S(=O)(=O)N(C)C)S1 PNVGYZVQSJWYQJ-UHFFFAOYSA-N 0.000 description 1
- YXKAWGJFXRNOIO-UHFFFAOYSA-N 5-amino-n,n-diethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=NN=C(N)S1 YXKAWGJFXRNOIO-UHFFFAOYSA-N 0.000 description 1
- NEKGFZXLZYSKQX-UHFFFAOYSA-N 5-amino-n,n-dimethyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=NN=C(N)S1 NEKGFZXLZYSKQX-UHFFFAOYSA-N 0.000 description 1
- NNCYCUBNBHNHHW-UHFFFAOYSA-N 5-amino-n-butyl-n-methyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound CCCCN(C)S(=O)(=O)C1=NN=C(N)S1 NNCYCUBNBHNHHW-UHFFFAOYSA-N 0.000 description 1
- INOOBKGATOFAEV-UHFFFAOYSA-N 5-amino-n-methyl-n-prop-2-ynyl-1,3,4-thiadiazole-2-sulfonamide Chemical compound C#CCN(C)S(=O)(=O)C1=NN=C(N)S1 INOOBKGATOFAEV-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- SWMGXKSQWDSBKV-UHFFFAOYSA-N Buthidazole Chemical compound O=C1N(C)CC(O)N1C1=NN=C(C(C)(C)C)S1 SWMGXKSQWDSBKV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000736839 Chara Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 244000038012 Fimbristylis barbata Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 240000001931 Ludwigia octovalvis Species 0.000 description 1
- 235000012629 Mentha aquatica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000061667 Myriophyllum aquaticum Species 0.000 description 1
- 235000004234 Myriophyllum brasiliense Nutrition 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- 241000721619 Najas Species 0.000 description 1
- 235000015225 Panicum colonum Nutrition 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000757039 Pontederiaceae Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- KZXIQMSWVSTGQX-UHFFFAOYSA-N SC1=CN=NS1 Chemical compound SC1=CN=NS1 KZXIQMSWVSTGQX-UHFFFAOYSA-N 0.000 description 1
- 241000195663 Scenedesmus Species 0.000 description 1
- 241000192589 Synechococcus elongatus PCC 7942 Species 0.000 description 1
- 240000001398 Typha domingensis Species 0.000 description 1
- IFMJXAIUDUOJLC-UHFFFAOYSA-N [3-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1-methyl-2-oxoimidazolidin-4-yl] acetate Chemical compound S1C(S(=O)(=O)N(C)C)=NN=C1N1C(=O)N(C)CC1OC(C)=O IFMJXAIUDUOJLC-UHFFFAOYSA-N 0.000 description 1
- YGIGSNJKNQKNGV-UHFFFAOYSA-N [3-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1-methyl-2-oxoimidazolidin-4-yl] n-methylcarbamate Chemical compound CNC(=O)OC1CN(C)C(=O)N1C1=NN=C(S(=O)(=O)N(C)C)S1 YGIGSNJKNQKNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000001856 aerosol method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000008624 imidazolidinones Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- HGWZXKUBDUDGSN-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)aniline Chemical compound COC(OC)CNC1=CC=CC=C1 HGWZXKUBDUDGSN-UHFFFAOYSA-N 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- KDAHOACMCMWJCL-UHFFFAOYSA-N phenyl n-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=NNC(=S)S1 KDAHOACMCMWJCL-UHFFFAOYSA-N 0.000 description 1
- IUCVXAKUFHZHMA-UHFFFAOYSA-N phenyl n-(5-chlorosulfonyl-1,3,4-thiadiazol-2-yl)carbamate Chemical compound S1C(S(=O)(=O)Cl)=NN=C1NC(=O)OC1=CC=CC=C1 IUCVXAKUFHZHMA-UHFFFAOYSA-N 0.000 description 1
- YLUMONCTUIFASP-UHFFFAOYSA-N phenyl n-[5-[ethyl(methyl)sulfamoyl]-1,3,4-thiadiazol-2-yl]carbamate Chemical compound S1C(S(=O)(=O)N(C)CC)=NN=C1NC(=O)OC1=CC=CC=C1 YLUMONCTUIFASP-UHFFFAOYSA-N 0.000 description 1
- LFZPOEYDYWHUCS-UHFFFAOYSA-N phenyl n-[5-[methyl(prop-2-ynyl)sulfamoyl]-1,3,4-thiadiazol-2-yl]carbamate Chemical compound S1C(S(=O)(=O)N(CC#C)C)=NN=C1NC(=O)OC1=CC=CC=C1 LFZPOEYDYWHUCS-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
- IZBAXOUZLXYCRJ-UHFFFAOYSA-N thiadiazol-4-ylcarbamic acid Chemical compound OC(=O)NC1=CSN=N1 IZBAXOUZLXYCRJ-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 238000009736 wetting Methods 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37413782A | 1982-05-03 | 1982-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8311822D0 GB8311822D0 (en) | 1983-06-02 |
| GB2119252A true GB2119252A (en) | 1983-11-16 |
Family
ID=23475466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08311822A Withdrawn GB2119252A (en) | 1982-05-03 | 1983-04-29 | Use of thiadiazolylimidazolidinones to control aquatic vegetation |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0094181A1 (enExample) |
| JP (1) | JPS58203905A (enExample) |
| DK (1) | DK194683A (enExample) |
| GB (1) | GB2119252A (enExample) |
| GR (1) | GR78541B (enExample) |
| IL (1) | IL68499A0 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600430A (en) * | 1985-02-22 | 1986-07-15 | Eli Lilly And Company | Pyridinylimidazolidinone compounds |
| US4604127A (en) * | 1984-07-17 | 1986-08-05 | Eli Lilly And Company | Herbicidal pyridazinylimidazolidinone compounds |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU581763B2 (en) * | 1985-06-14 | 1989-03-02 | Ppg Industries, Inc. | Herbicidal imidazolidinone derivatives |
| US9210930B2 (en) | 2005-12-23 | 2015-12-15 | Basf Se | Control of submerged aquatic vegetation |
| US8080497B2 (en) | 2005-12-23 | 2011-12-20 | Basf Se | Method of controlling the aquatic weed Hydrilla verticillata |
| US9060516B2 (en) | 2005-12-23 | 2015-06-23 | Basf Se | Method for controlling aquatic weeds |
-
1983
- 1983-04-27 IL IL68499A patent/IL68499A0/xx unknown
- 1983-04-28 GR GR71245A patent/GR78541B/el unknown
- 1983-04-29 EP EP83302430A patent/EP0094181A1/en not_active Withdrawn
- 1983-04-29 GB GB08311822A patent/GB2119252A/en not_active Withdrawn
- 1983-05-02 JP JP58078842A patent/JPS58203905A/ja active Pending
- 1983-05-02 DK DK194683A patent/DK194683A/da not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604127A (en) * | 1984-07-17 | 1986-08-05 | Eli Lilly And Company | Herbicidal pyridazinylimidazolidinone compounds |
| US4600430A (en) * | 1985-02-22 | 1986-07-15 | Eli Lilly And Company | Pyridinylimidazolidinone compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58203905A (ja) | 1983-11-28 |
| GB8311822D0 (en) | 1983-06-02 |
| DK194683A (da) | 1983-11-04 |
| EP0094181A1 (en) | 1983-11-16 |
| DK194683D0 (da) | 1983-05-02 |
| GR78541B (enExample) | 1984-09-27 |
| IL68499A0 (en) | 1983-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0087780B1 (en) | Pyrazolesulfonylurea derivative, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof | |
| AU601656B2 (en) | Pesticidal polyhaloalkene derivatives | |
| US3770754A (en) | Certai 1,2,4-oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives | |
| US4042372A (en) | Substituted thiadiazolotriazinediones and method of preparation | |
| GB2084140A (en) | Herbicidal n-arylbenzamide derivatives | |
| JPS6391378A (ja) | アミノピラジノン及びアミノトリアジノン、それらの製造方法並びにそれらを含有する組成物 | |
| EP0244098A2 (en) | Thiazolotriazole herbicides | |
| DD231717A5 (de) | Herbizide bzw. fungizide mittel | |
| KR800000505B1 (ko) | 1-티아디아 졸리이미다 졸리딘온의 제조방법 | |
| US4576629A (en) | Herbicidal thiadiazole ureas | |
| US4354030A (en) | Isoxazolylimidazolidinone herbicides | |
| US3967950A (en) | Combating weeds in rice with benzothiazole derivatives | |
| JPS6013771A (ja) | イソチアゾリルウレア類 | |
| EP0044185A2 (en) | Imidazolidinone derivatives | |
| GB2119252A (en) | Use of thiadiazolylimidazolidinones to control aquatic vegetation | |
| GB2043062A (en) | N-(heterocyclyl)-acetanilide derivatives and herbicidal and plant growth regulating compositions containing them | |
| AU659647B2 (en) | Substituted benzothiazole derivatives, their preparation and use as herbicides | |
| EP0003539A2 (de) | N-Azolylalkyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide | |
| US5670456A (en) | Compounds | |
| JPH0242070A (ja) | 植物生長調節剤としての1,2,3―ベンゾチアジアゾール―4―カルボン酸誘導体 | |
| US4056382A (en) | Method of controlling aquatic weeds | |
| JPH02178277A (ja) | 2,5―二置換1,3,4―チアジアゾール誘導体、それらの製造方法、及び有害生物防除剤におけるそれらの使用 | |
| USRE29439E (en) | Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives | |
| 萩原健司 et al. | Synthesis and herbicidal activity of fused Δ 2-1, 2, 4-thiadiazolines | |
| US4911749A (en) | Aquatic herbicidal methods |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |