WO1998042703A1 - Thiazolimin-derivate - Google Patents
Thiazolimin-derivate Download PDFInfo
- Publication number
- WO1998042703A1 WO1998042703A1 PCT/EP1998/001442 EP9801442W WO9842703A1 WO 1998042703 A1 WO1998042703 A1 WO 1998042703A1 EP 9801442 W EP9801442 W EP 9801442W WO 9842703 A1 WO9842703 A1 WO 9842703A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- halogen
- groups
- formula
- alkoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 66
- 150000002367 halogens Chemical class 0.000 claims abstract description 66
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 3
- -1 thiazole imines Chemical class 0.000 claims description 95
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- XKHZAKWFNZMTHJ-UHFFFAOYSA-N n-(1,3-thiazol-1-ylidene)acetamide Chemical class CC(=O)N=S1C=CN=C1 XKHZAKWFNZMTHJ-UHFFFAOYSA-N 0.000 claims description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- DUBPQMVNXGXBKM-UHFFFAOYSA-N 3-(2,2-difluoro-1,3-benzodioxol-4-yl)-5-methyl-1,3-thiazol-2-imine;hydrochloride Chemical compound Cl.N=C1SC(C)=CN1C1=CC=CC2=C1OC(F)(F)O2 DUBPQMVNXGXBKM-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000021533 Beta vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 0 CC(*)(*C(C)=*C)N Chemical compound CC(*)(*C(C)=*C)N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920005610 lignin Polymers 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QPXDKQBBJCTNOY-UHFFFAOYSA-N 1,10-phenanthrolin-10-ium;chloride Chemical compound Cl.C1=CN=C2C3=NC=CC=C3C=CC2=C1 QPXDKQBBJCTNOY-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- 125000006073 1-ethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 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
- 125000001624 naphthyl group Chemical group 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AMMGCGVWJMRTQI-UHFFFAOYSA-N prop-1-en-2-yl carbonochloridate Chemical compound CC(=C)OC(Cl)=O AMMGCGVWJMRTQI-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 210000000614 rib Anatomy 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Definitions
- the present invention relates to new thiazolimine derivatives with herbicidal activity, a process for the preparation of the thiazolimine derivatives, compositions which contain them and the use of these derivatives or compositions containing them for weed control.
- Herbicidal thiazolimine derivatives are known from the literature (US Pat. No. 5,244,863; EP 529 482, EP 446 802).
- the task was to find new thiazolimine derivatives with improved properties.
- X, Y independently of one another hydrogen, halogen, -CC 4 alkyl, -C 4 -haloalkyl;
- C ⁇ -C 8 alkyl C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C ⁇ -C 8 -alkoxy, C 8 alkylthio, where these groups substituted by one to five halogen or C_-C 4 Alkoxy can be substituted;
- C 1 -C 4 -alkyl, C_-C 4 -alkoxy, C_-C 4 -haloalkyl, C_-C 4 -haloalkoxy, halogen, nitro or cyano may be substituted; or one of the following groups: R 3 ; S R6;
- R 1 , R 2 are hydrogen, halogen
- R 3 is hydrogen
- R 4 , R 5 are hydrogen
- Groups can be substituted by one to four halogen or by C_-C 4 alkoxy;
- C 1 -C 4 alkoxy, C 1 -C haloalkoxy may be substituted
- Nitro or cyano can be substituted;
- R 4 , R 5 together form a 3- to 7-membered heterocycle which can carry a further heteroatom of N, 0 or S, can contain at least one double bond and with C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 -alkoxy, C_-C 4 -haloalkoxy, halogen, nitro or cyano groups may be substituted;
- R 6 is hydrogen
- Ci-C ⁇ -alkyl C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, where these groups can be substituted by one to four halogen or by alkoxy;
- C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkenyl, the foundation with one to four halogen atoms or C_-C 4 - alkyl, C ⁇ -C 4 -Halo- alkyl, C 1 -C 4 alkoxy, haloalkoxy substituted could be;
- anilines of the formula II which are known from DE 41 33 156, are used in the presence of an organic or inorganic base in a ratio of 0.5 to 5 equivalents with substituted propargyl derivatives of the general Formula III reacted in an inert solvent at temperatures between 0 and 100 ° C.
- LG stands for a nucleophilically exchangeable leaving group such as halogen, mesylate, tosylate or acetate.
- the reaction is generally carried out by adding the alkylating agent to the aniline derivative of the general formula II and the base.
- Suitable bases are tertiary amines, pyridine, the aniline derivative of the general formula II or potassium carbonate and cesium carbonate, which are used in a range from 0.5 to 5 molar equivalents.
- methylene chloride, chloroform, dioxane, tetrahydrofuran, dimethylformamide, acetonitrile, toluene or ethyl acetate can be used as solvents.
- the reaction mixture is preferably stirred at a temperature between 0 and 150 ° C.
- the processing takes place in the usual way, e.g. the reaction mixture is poured into water and the product of value is extracted by extraction with, for example, methylene chloride. Further purification can be carried out, for example, by chromatography, crystallization or distillation. (Organikum, 16th edition, VEB German Publishing House of Sciences, Berlin 1986; J. Fluorine Chem. 1993, 60, 31-38)
- the reaction is generally carried out by adding the aniline derivative of the general formula IV to a reaction mixture of KSCN and acetyl chloride in an inert solvent such as methylene chloride, chloroform, dioxane, tetrahydrofuran, dimethylformamide, acetonitrile, toluene or ethyl acetate.
- an inert solvent such as methylene chloride, chloroform, dioxane, tetrahydrofuran, dimethylformamide, acetonitrile, toluene or ethyl acetate.
- reaction mixture is poured onto water and the product of value is separated off by extraction with, for example, methylene chloride.
- the further implementation takes place after drying.
- the reaction mixture is either dissolved in an inert solvent such as methylene chloride, chloroform, tetrahydrofuran, ethyl acetate or reacted in bulk with an auxiliary reagent.
- the temperature is in a range between -15 ° C and 150 ° C.
- the catalyst can be an inorganic acid such as sulfuric acid, hydrochloric acid, phosphoric acid, an organic acid such as acetic acid, trifluoroacetic acid, toluenesulfonic acid, a base such as potassium tert. -butylate, sodium methoxide, pyridine, triethylamine, dimethylaminopyridine.
- working up is carried out in the customary manner, for example the reaction mixture is poured into water and the product of value is then separated off by extraction with, for example, methylene chloride.
- the cleaning can be carried out by crystallization or chromatography (EP 446 802).
- N-acetylthiazolimines of the general formula VIII are converted into their salts by acid hydrolysis.
- N-acetylthiazolimines of the general formula VIII are generally dissolved in an inert organic solvent such as methylene chloride, chloroform, tetrahydrofuran, dimethylformamide, toluene, diethyl ether, methanol, ethanol and reacted with 1 to 100 equivalents of an organic or inorganic acid brought.
- the temperature is usually between 0 and 150 ° C.
- Suitable acids are organic and inorganic acids such as acetic acid, trifluoroacetic acid, p- Toluenesulfonic acid or sulfuric acid, hydrochloric acid and phosphoric acid.
- the processing is generally carried out in such a way that the solvent is removed in vacuo and the salt which remains is purified by crystallization from an inert solvent (T.W. Greene, Protective Groups in Organic Synthesis, Wiley, InterScience, N.Y.).
- an inert solvent T.W. Greene, Protective Groups in Organic Synthesis, Wiley, InterScience, N.Y.
- LG stands for a nucleophilically exchangeable leaving group such as halogen, mesylate, tosylate or acetate.
- N-substituted thiazolimine derivatives of the general formula I are generally in an inert solvent such as, for example, methylene chloride, chloroform, tetrahydrofuran, dimethylformamide, toluene, diethyl ether, ethyl acetate, methanol or ethanol by reacting thiazolimine derivatives of the general formula IX with one to ten Equivalents of an organic base and subsequent reaction with one to ten equivalents of the radical Z, which carries a leaving group (LG).
- Halogen atoms, ester groups and OH groups are particularly suitable as leaving groups.
- dehydrating agents such as dicyclohexylcarbodiimide and related substances can be added to the reaction.
- the temperature during the reaction is in a range between -15 ° C and + 100 ° C.
- the up work is generally carried out so that the reaction mixture is poured into water and the product of value is then extracted with an organic solvent such as methylene chloride or ethyl acetate.
- the product of value can be purified by chromatography, distillation or crystallization.
- Halogen fluorine, chlorine, bromine and iodine
- Alkyl straight-chain or branched alkyl group with 1 to 4, 6, 8 or 10 carbon atoms, for example Ci-C ⁇ - alkyl w methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, Methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1- Methylpentyl, 2-methyl pentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl,
- Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-C0-);
- Halo ⁇ enalkyl straight-chain or branched alkyl groups with 1 to 4 carbon atoms, in which groups the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, Chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, -
- Haloalkenoxy straight-chain or branched alkyl groups with 1 to 4 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, and where these groups are bonded to the skeleton via an oxygen atom;
- Alkylthio straight-chain or branched alkyl groups with 1 to 4, 6 or 8 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), for example C_-C 6 -alkylthio such as methylthio, ethylthio, propylthio, 1- Methyl-ethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-di-methylpropylthio, 1-ethylpropylthio, Hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-d
- Cvcloalky monocyclic alkyl groups with 3 to 7 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl;
- Cycloalkenyl as under cycloalkyl with at least one double bond
- Alkenyl straight-chain or branched alkenyl groups with 2 to 6, 8 or 10 carbon atoms and a double bond in any position, for example CC 6 ⁇ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4 -Pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2-propeny
- Alkenylcarbonyl straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position, which are bonded to the skeleton via a carbonyl group (-C0-);
- Alkynyl straight-chain or branched alkynyl groups with 2 to 8 or 10 carbon atoms and a triple bond in any position, for example CC 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2 -Pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2 propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl
- Alkynylcarbonyl straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-C0-);
- Aryl aromatic mono- or polycyclic hydrocarbon residues e.g. Phenyl, naphthyl and phenanthrenyl;
- Hetaryl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, for example 5- ⁇ liedri ⁇ es heteroaryl, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5 -Pyrazolyl, 2-imidazolyl, 4-imidazolyl, l, 2,4-triazol-3-yl and 1, 3, 4-triazol-2-yl;
- 5- ⁇ liedri ⁇ es heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three May contain nitrogen atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-oxazolyl, 5-0xazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,
- benzo-fused 5- ⁇ liedri ⁇ es heteroaryl containing one to three nitrogen atoms or a nitrogen atom and / or an oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur atom
- 6- ⁇ liedri ⁇ es heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups, which in addition to carbon atoms can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3, 5-triazin-2-yl, 1, 2, 4-triazin-3-yl and 1,2,4,5-etrazin-3 -y1;
- 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
- Cx-Cs alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, -C-C 8 alkoxy, C_-C 8 alkylthio means, these groups by one to five halogen atoms or C 1 -C 4 -alkoxy may be substituted; or stands for one of the following groups: OR 3
- Z represents one of the following groups:
- R i , R 2 hydrogen, halogen
- Rl is hydrogen, halogen or C 1 -C 4 alkyl
- R 2 is hydrogen, halogen
- C1-C 4 alkyl which can be substituted by one to five halogen atoms, mean.
- R represents methyl or ethyl.
- R3 C ⁇ -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 2 -C 8 alkyl carbonyl, these groups being substituted by one to eight halogen or by C 1 -C 4 - Alkoxy may be substituted;
- Aryl which can be substituted by C 1 -C 4 alkyl, C_-C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, haloagen,
- Cycloalkyl which can be substituted by one to eight halogen atoms, C 1 -C 4 -alkyl or C_-C 4 -haloalkyl,
- R 4 , R 5 are hydrogen; -C-C 6 alkyl, C 2 -C 6 alkenyl, C -C 6 "alkynyl, where these groups can be substituted by one to four halogen or by C 1 -C 4 alkoxy;
- Aryl which can be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, Ci-haloalkyl, C 1 -C 4 -haloalkoxy or halogen,
- R 4 , R 5 together form a 3- to 7-membered heterocycle which can carry a further hetero atom of N, 0 or S, can contain a double bond and with one to four C_-C 4 -alkyl, C ⁇ -C 4 - Haloalkyl, -C-C 4 alkoxy, C_-C 4 halo alkoxy, halogen, nitro or cyano groups can be substituted.
- R 4 , R 5 are hydrogen or C_-C 6 alkyl, which can be substituted by one to four halogen,
- R, R 5 together form a 3- to 7-membered heterocycle which can carry a further heteroatom from N, 0 or S, can contain a double bond and can be substituted by C_-C 4 -alkyl.
- R 6 is hydrogen
- C 3 -C cycloalkyl which can be substituted by one to four halogen or C_-C 4 alkyl, C_-C 4 haloalkyl, C 1 -C 4 alkoxy, haloalkoxy;
- Aryl hetaryl, these groups being substituted by C 1 -C 4 alkyl,
- C_-C 4 -haloalkyl, C ⁇ -C 4 -alkoxy, C_-C_ -haloalkoxy, halogen, nitro or cyano may be substituted
- n 1
- n 2
- Oxygen atom of the heterocycle is linked to the benzene ring.
- X, Y independently of one another are hydrogen, halogen or C 1 -C 4 -alkyl
- Z is hydrogen; C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C_-C 8 -alkoxy,
- R, R 2 are hydrogen, halogen
- C 3 -C 7 cycloalkyl, 4 alkyl or C ⁇ -C 4 haloalkyl may be substituted by one to eight halogen atoms, C 1 -C 4 alkoxy, C 1 -C;
- Aryl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or halogen may be substituted by C ⁇ -C alkyl, C_-C 4 haloalkyl;
- R 4 , R 5 are hydrogen
- C 1 -C 4 alkoxy may be substituted
- Aryl which can be substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C_-C 4 haloalkyl, C 1 -C 4 haloalkoxy or halogen;
- R 4 , R 5 together form a 3- to 7-membered heterocycle, which can carry a further heteroatom from N, 0 or S, can contain a double bond and with C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, halogen, nitro or cyano groups;
- R 6 is hydrogen; Ci-C ⁇ -alkyl or C 2 -C 6 alkenyl, where these groups can be substituted by one to four halogen or by alkoxy;
- C 3 -C 7 cycloalkyl which can be substituted by one to four halogen atoms, C 1 -C alkyl, C_-C 4 haloalkyl, C_-C 4 alkoxy or haloalkoxy;
- Aryl or hetaryl, where these groups can be substituted by C_-C 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy, C 1 -C 4 -haloalkoxy, halogen, nitro or cyano;
- X, Y independently of one another are hydrogen or halogen
- R 1 is hydrogen, halogen or C_ -C alkyl
- R 2 is hydrogen, halogen
- R 3 is C_-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl or
- C 2 -C 8 alkylcarbonyl where these groups can be substituted by one to eight halogen;
- C 3 -C cycloalkyl which may be substituted by one to eight halogen atoms, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
- R 4 , R 5 are hydrogen
- R 4 , R 5 together form a 3- to 7-membered heterocycle which can carry a further heteroatom from N, 0 or S, can contain a double bond and can be substituted by C 1 -C 4 alkyl;
- R 2 is methyl or ethyl
- C 3 -C cycloalkyl which can be substituted by one to eight halogen atoms, C 1 -C 4 alkyl or -C-C 4 haloalkyl;
- R 4 , R 5 are hydrogen
- C_-C 6 alkyl which can be substituted by one to four halogen atoms, or
- R, R 5 together form a 3- to 7-membered heterocycle which can carry a further heteroatom from N, 0 or S, can contain a double bond and can be substituted by C 1 -C alkyl;
- R 1 is water
- R 2 is methyl and the substituent Z corresponds to one row of Table A for each individual compound.
- R 1 is hydrogen
- R 2 is methyl and the substituent Z corresponds to one row of Table A for each individual compound.
- R 1 is hydrogen
- R 2 is methyl and the substituent Z corresponds to one row of Table A for each individual compound.
- R i is hydrogen
- R 2 is methyl and the substituent Z corresponds to one row of Table A for each individual compound.
- R i is hydrogen
- R 2 is methyl and the substituent Z corresponds to one row of Table A for each individual compound.
- the organic phases are washed 3 times with water and 1 time with saturated NaCl solution and then dried over Na 2 S0 4 .
- the residue obtained after evaporation of the solvent is concentrated at 0 ° C to 61 ml.
- the solution is then poured onto ice water and neutralized with 50% sodium hydroxide solution at 20-25 ° C.
- the aqueous phase is then extracted 3 times with methylene chloride and the combined organic phases are washed 2 times with water and 1 time with saturated NaCl solution. After the solvent has been dried and evaporated, the residue is recrystallized from diethyl ether.
- the precipitate which has separated out is filtered off with suction and the filtrate is washed 3 times with water and 1 time with saturated NaCl solution. After drying the org. Phase, the solvent is evaporated in vacuo and the residue is purified by column chromatography on silica gel using cyclohexane / ethyl acetate mixtures.
- the filtrate is washed 3 times with water and 1 time with saturated NaCl solution and then dried over Na 2 S0 4. After removing the solvent in vacuo, the residue is purified by column chromatography on silica gel using cyclohexane / ethyl acetate mixtures.
- the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
- the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
- the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
- the following crops are considered, for example:
- the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
- the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are, if possible not be hit while the active ingredients get on the leaves of unwanted plants growing underneath or the uncovered floor area (post-directed, lay-by).
- the compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
- the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
- Mineral oil fractions from medium to high boiling point such as kerosene or diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
- Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
- emulsions, pastes or oil dispersions the thiazolimine derivatives, or those dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
- concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
- the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenyl glycolphenyl, alkylphen -
- Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
- Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
- the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
- the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
- the compounds I according to the invention can be formulated, for example, as follows:
- I 20 parts by weight of compound no. 13.13 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzene sulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
- aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
- Parts by weight of water give an aqueous dispersion which contains 0.02% by weight of the active ingredient.
- V 3 parts by weight of active ingredient no. 13.13 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
- VIII 1 part by weight of compound 13.13 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (non-ionic Emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
- the thiazolimine derivatives can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
- 1,2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2-aroyl come as mixing partners -l, 3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives,
- the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also) Examples of use
- Plastic pots with loamy sand with about 3.0% humus served as the culture vessels.
- the seeds of the test plants were sown separately according to species.
- pre-emergence treatment the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
- the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
- the application rate for the pre-emergence treatment was 0.5 or 0.25 kg / ha a. S.
- test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water.
- the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
- the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
- the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
- Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
- the plants used in the greenhouse experiments are composed of the following types:
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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JP54481898A JP2001518918A (ja) | 1997-03-24 | 1998-03-12 | チアゾールイミン誘導体 |
CA002283925A CA2283925A1 (en) | 1997-03-24 | 1998-03-12 | Thiazolimine derivatives |
EP98912471A EP0973771A1 (de) | 1997-03-24 | 1998-03-12 | Thiazolimin-derivate |
US09/381,463 US6165943A (en) | 1997-03-24 | 1998-03-12 | Thiazolimine derivatives |
AU67294/98A AU6729498A (en) | 1997-03-24 | 1998-03-12 | Thiazolimine derivatives |
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Application Number | Priority Date | Filing Date | Title |
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DE19712226 | 1997-03-24 | ||
DE19712226.4 | 1997-03-24 |
Publications (1)
Publication Number | Publication Date |
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WO1998042703A1 true WO1998042703A1 (de) | 1998-10-01 |
Family
ID=7824395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP1998/001442 WO1998042703A1 (de) | 1997-03-24 | 1998-03-12 | Thiazolimin-derivate |
Country Status (8)
Country | Link |
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US (1) | US6165943A (de) |
EP (1) | EP0973771A1 (de) |
JP (1) | JP2001518918A (de) |
AR (1) | AR015576A1 (de) |
AU (1) | AU6729498A (de) |
CA (1) | CA2283925A1 (de) |
WO (1) | WO1998042703A1 (de) |
ZA (1) | ZA982436B (de) |
Cited By (5)
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WO2000042032A1 (de) * | 1999-01-12 | 2000-07-20 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
US6165943A (en) * | 1997-03-24 | 2000-12-26 | Basf Aktiengesellschaft | Thiazolimine derivatives |
WO2001010853A1 (de) * | 1999-08-10 | 2001-02-15 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
WO2008002956A2 (en) * | 2006-06-27 | 2008-01-03 | Abbott Laboratories | Thiazoline and oxazoline derivatives and their methods of use |
WO2009086163A3 (en) * | 2007-12-21 | 2009-09-03 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
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US20080312435A1 (en) * | 2004-11-15 | 2008-12-18 | Taisho Pharmaceutical Co., Ltd. | Imine Compound |
CN101448800A (zh) * | 2006-05-31 | 2009-06-03 | 艾博特公司 | 作为大麻素受体配体的新型化合物及其用途 |
US8546583B2 (en) * | 2006-05-31 | 2013-10-01 | Abbvie Inc. | Compounds as cannabinoid receptor ligands and uses thereof |
WO2009067613A1 (en) * | 2007-11-21 | 2009-05-28 | Abbott Laboratories | Novel compounds as cannabinoid receptor ligands and uses thereof |
US20110108199A1 (en) * | 2009-11-10 | 2011-05-12 | Tyco Healthcare Group Lp | Hemostatic Tapes and Dispensers Therefor |
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1998
- 1998-03-12 AU AU67294/98A patent/AU6729498A/en not_active Abandoned
- 1998-03-12 CA CA002283925A patent/CA2283925A1/en not_active Abandoned
- 1998-03-12 US US09/381,463 patent/US6165943A/en not_active Expired - Fee Related
- 1998-03-12 WO PCT/EP1998/001442 patent/WO1998042703A1/de not_active Application Discontinuation
- 1998-03-12 JP JP54481898A patent/JP2001518918A/ja active Pending
- 1998-03-12 EP EP98912471A patent/EP0973771A1/de not_active Withdrawn
- 1998-03-23 ZA ZA9802436A patent/ZA982436B/xx unknown
- 1998-03-24 AR ARP980101336A patent/AR015576A1/es unknown
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6165943A (en) * | 1997-03-24 | 2000-12-26 | Basf Aktiengesellschaft | Thiazolimine derivatives |
WO2000042032A1 (de) * | 1999-01-12 | 2000-07-20 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
WO2001010853A1 (de) * | 1999-08-10 | 2001-02-15 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
WO2008002956A2 (en) * | 2006-06-27 | 2008-01-03 | Abbott Laboratories | Thiazoline and oxazoline derivatives and their methods of use |
WO2008002956A3 (en) * | 2006-06-27 | 2008-07-03 | Abbott Lab | Thiazoline and oxazoline derivatives and their methods of use |
US7683084B2 (en) | 2006-06-27 | 2010-03-23 | Abbott Laboratories | Thiazoline and oxazoline derivatives and their methods of use |
US8470813B2 (en) | 2006-06-27 | 2013-06-25 | Abbvie Inc. | Thiazoline and oxazoline derivatives and their methods of use |
WO2009086163A3 (en) * | 2007-12-21 | 2009-09-03 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
JP2011508734A (ja) * | 2007-12-21 | 2011-03-17 | アボット・ラボラトリーズ | チアゾリリジン尿素およびアミド誘導体ならびにこの使用方法 |
US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
Also Published As
Publication number | Publication date |
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JP2001518918A (ja) | 2001-10-16 |
US6165943A (en) | 2000-12-26 |
CA2283925A1 (en) | 1998-10-01 |
ZA982436B (en) | 1999-09-23 |
AU6729498A (en) | 1998-10-20 |
AR015576A1 (es) | 2001-05-16 |
EP0973771A1 (de) | 2000-01-26 |
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