JP2005516973A - 除草剤として有用なフェニル置換ヘテロ環化合物 - Google Patents
除草剤として有用なフェニル置換ヘテロ環化合物 Download PDFInfo
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- JP2005516973A JP2005516973A JP2003562121A JP2003562121A JP2005516973A JP 2005516973 A JP2005516973 A JP 2005516973A JP 2003562121 A JP2003562121 A JP 2003562121A JP 2003562121 A JP2003562121 A JP 2003562121A JP 2005516973 A JP2005516973 A JP 2005516973A
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- Prior art keywords
- alkyl
- haloalkyl
- alkenyl
- alkoxy
- substituted
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- -1 C 2 -C 5 haloalkenyl Chemical group 0.000 claims description 138
- 239000001257 hydrogen Substances 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 229910052736 halogen Inorganic materials 0.000 claims description 91
- 150000002367 halogens Chemical class 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 239000001301 oxygen Chemical group 0.000 claims description 51
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 50
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 230000002363 herbicidal effect Effects 0.000 claims description 43
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 229910052717 sulfur Chemical group 0.000 claims description 39
- 239000011593 sulfur Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 31
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 25
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 20
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 20
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 230000008635 plant growth Effects 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- RGTVXXNMOGHRAY-WDSKDSINSA-N Cys-Arg Chemical group SC[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N RGTVXXNMOGHRAY-WDSKDSINSA-N 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 230000008485 antagonism Effects 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
- 125000004969 haloethyl group Chemical group 0.000 claims description 3
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 77
- 150000002431 hydrogen Chemical class 0.000 description 73
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 241000196324 Embryophyta Species 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 27
- 239000004094 surface-active agent Substances 0.000 description 27
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 23
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 20
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
- 239000002736 nonionic surfactant Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
- 238000004611 spectroscopical analysis Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 11
- 239000000654 additive Substances 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000003945 anionic surfactant Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 0 C*1*(C)C(ON)=C(C)C1O Chemical compound C*1*(C)C(ON)=C(C)C1O 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000003093 cationic surfactant Substances 0.000 description 8
- 235000009973 maize Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 235000015112 vegetable and seed oil Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 244000045561 useful plants Species 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 5
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 description 5
- QHUWVQWAKAJLTJ-UHFFFAOYSA-N 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydropyrazolo[1,2-d][1,4,5]oxadiazepine-7,9-dione Chemical compound CCC1=CC(C)=CC(CC)=C1C1C(=O)N2CCOCCN2C1=O QHUWVQWAKAJLTJ-UHFFFAOYSA-N 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000009331 sowing Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000012669 liquid formulation Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000743339 Agrostis Species 0.000 description 3
- 241000743985 Alopecurus Species 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 241000209200 Bromus Species 0.000 description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000000729 antidote Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007931 coated granule Substances 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
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- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- LYNULMGRTLBOCI-UHFFFAOYSA-N n-(4-acetamidophenyl)sulfonyl-2-(trifluoromethoxy)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC(F)(F)F LYNULMGRTLBOCI-UHFFFAOYSA-N 0.000 description 1
- KDBZITFPRDFMHZ-UHFFFAOYSA-N n-(4-acetamidophenyl)sulfonyl-2-(trifluoromethyl)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1C(F)(F)F KDBZITFPRDFMHZ-UHFFFAOYSA-N 0.000 description 1
- VLWAYARFKONSPF-UHFFFAOYSA-N n-(4-acetamidophenyl)sulfonyl-2-chlorobenzamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1Cl VLWAYARFKONSPF-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- DODKLLYJAZAJFX-UHFFFAOYSA-N n-[4-(cyclobutanecarbonylamino)phenyl]sulfonyl-2-(trifluoromethoxy)benzamide Chemical group FC(F)(F)OC1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CCC1 DODKLLYJAZAJFX-UHFFFAOYSA-N 0.000 description 1
- GPNFWMGMKZUMHD-UHFFFAOYSA-N n-[4-(cyclobutanecarbonylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CCC1 GPNFWMGMKZUMHD-UHFFFAOYSA-N 0.000 description 1
- MVSXAWABXDPICZ-UHFFFAOYSA-N n-[4-(cyclopropanecarbonylamino)phenyl]sulfonyl-2-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CC1 MVSXAWABXDPICZ-UHFFFAOYSA-N 0.000 description 1
- WUWIKZVMPNSGCK-UHFFFAOYSA-N n-[4-(cyclopropanecarbonylamino)phenyl]sulfonyl-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CC1 WUWIKZVMPNSGCK-UHFFFAOYSA-N 0.000 description 1
- LWKQIRXCWZMQNM-UHFFFAOYSA-N n-[4-(cyclopropanecarbonylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CC1 LWKQIRXCWZMQNM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- IUZZLNVABCISOI-UHFFFAOYSA-N n-ethylheptan-1-amine Chemical compound CCCCCCCNCC IUZZLNVABCISOI-UHFFFAOYSA-N 0.000 description 1
- SDQCOADWEMMSGK-UHFFFAOYSA-N n-ethyloctan-1-amine Chemical compound CCCCCCCCNCC SDQCOADWEMMSGK-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
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- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
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- CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 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
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229930000184 phytotoxin Natural products 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 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
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1192002 | 2002-01-22 | ||
| PCT/EP2003/000555 WO2003062244A1 (en) | 2002-01-22 | 2003-01-21 | Phenyl substituted heterocyclic compounds useful as herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005516973A true JP2005516973A (ja) | 2005-06-09 |
| JP2005516973A5 JP2005516973A5 (https=) | 2005-12-22 |
Family
ID=27587784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003562121A Pending JP2005516973A (ja) | 2002-01-22 | 2003-01-21 | 除草剤として有用なフェニル置換ヘテロ環化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050090399A1 (https=) |
| EP (1) | EP1468000A1 (https=) |
| JP (1) | JP2005516973A (https=) |
| CN (1) | CN1615310A (https=) |
| BR (1) | BR0306957A (https=) |
| CA (1) | CA2470674A1 (https=) |
| HU (1) | HUP0402592A2 (https=) |
| MX (1) | MXPA04006991A (https=) |
| RU (1) | RU2004125878A (https=) |
| WO (1) | WO2003062244A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013536818A (ja) * | 2010-09-01 | 2013-09-26 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 除草活性を有するケトスルタム類及びジケトピリジン類 |
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| DE10311300A1 (de) * | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE10326386A1 (de) * | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE10337497A1 (de) | 2003-08-14 | 2005-03-10 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate |
| JP2005154298A (ja) * | 2003-11-21 | 2005-06-16 | Idemitsu Kosan Co Ltd | 第三級カルボン酸 |
| DE102004014620A1 (de) * | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| DE102004035133A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
| DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
| DE102005059469A1 (de) | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
| DE102006000971A1 (de) * | 2006-01-07 | 2007-07-12 | Bayer Cropscience Ag | 2,4,6-Trialkylphenylsubstituierte Cyclopentan-1,3-dione |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| DE102006018828A1 (de) | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| EP2014169A1 (de) | 2007-07-09 | 2009-01-14 | Bayer CropScience AG | Wasserlösliche Konzentrate von 3-(2-Alkoxy-4-chlor-6-alkyl-phenyl)-substituierten Tetramaten und ihren korrespondierenden Enolen |
| EP2020413A1 (de) | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
| EP2045240A1 (de) | 2007-09-25 | 2009-04-08 | Bayer CropScience AG | Halogenalkoxyspirocyclische Tetram- und Tetronsäure-Derivate |
| EP2095710A1 (de) * | 2008-02-27 | 2009-09-02 | Bayer CropScience AG | Herbizid-Kombinationen enthaltend Diflufenican |
| EP2103615A1 (de) | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclisch substituierte Tetramate |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US8367873B2 (en) * | 2008-10-10 | 2013-02-05 | Bayer Cropscience Ag | Phenyl-substituted bicyclooctane-1,3-dione derivatives |
| TW201031327A (en) * | 2008-11-14 | 2010-09-01 | Bayer Cropscience Ag | Active compound combinations having insecticidal and acaricidal properties |
| US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| ES2342997B1 (es) | 2008-12-09 | 2011-06-06 | Universitat De Les Illes Balears | Alpha derivados de acidos grasos cis-monoinsaturados para ser usados como medicamento. |
| AR075126A1 (es) | 2009-01-29 | 2011-03-09 | Bayer Cropscience Ag | Metodo para el mejor uso del potencial de produccion de plantas transgenicas |
| CN102348684B (zh) | 2009-03-11 | 2014-11-12 | 拜尔农作物科学股份公司 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
| DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| CN103068825A (zh) | 2010-02-10 | 2013-04-24 | 拜耳知识产权有限责任公司 | 螺杂环取代的特特拉姆酸衍生物 |
| WO2011098440A2 (de) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Biphenylsubstituierte cyclische ketoenole |
| DE102010008642A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| DE102010008643A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| EP2560487A1 (de) | 2010-04-20 | 2013-02-27 | Bayer Intellectual Property GmbH | Insektizide und/oder herbizide zusammensetzung mit verbesserter wirkung auf basis von spiroheterocyclisch-substituierten tetramsäure-derivaten |
| BR112013010810A2 (pt) | 2010-11-02 | 2016-08-09 | Bayer Ip Gmbh | derivados de fenil-substituído bicicloocteno-1, 3-diona. |
| BR112013018973A2 (pt) | 2011-01-25 | 2017-09-19 | Bayer Ip Gmbh | processo para a preparação de derivados de 1-h-pirrolidina-2,4-diona |
| DE102011011040A1 (de) | 2011-02-08 | 2012-08-09 | Bayer Pharma Aktiengesellschaft | (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie |
| DE102011080405A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur Therapie |
| BR112013021021A2 (pt) | 2011-02-17 | 2016-08-02 | Bayer Ip Gmbh | 3- (bifenil - 3 - il) - 8, 8 - difluoro - 4 - hidroxi - 1 - azaspiro [4, 5] dec - 3 - eno - 2 - onas substituídas para terapia e cetoenóis espirocíclicos substituídos com halogéneo |
| KR101789527B1 (ko) | 2011-03-01 | 2017-10-25 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 2-아실옥시피롤린-4-온 |
| DE102011080406A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro8[4.5]dec-3-en-2-one |
| KR102030337B1 (ko) | 2012-01-26 | 2019-10-10 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 어류 기생충 방제용의 페닐-치환된 케토에놀 |
| NZ732707A (en) | 2014-12-18 | 2022-07-01 | Nissan Chemical Ind Ltd | Ketone or oxime compound, and herbicide |
| KR102671723B1 (ko) | 2016-01-15 | 2024-06-04 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 치환된 2-아릴에탄올의 제조 방법 |
| AU2019250592B2 (en) | 2018-04-13 | 2024-06-27 | Bayer Aktiengesellschaft | Use of tetramic acid derivatives for controlling pests by watering or droplet application |
| WO2019197652A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Feststoff-formulierung insektizider mischungen |
| WO2019197618A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
| WO2019197620A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
| WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
| EP3938349A1 (de) * | 2019-03-15 | 2022-01-19 | Bayer Aktiengesellschaft | Speziell substituierte 3-(2-alkoxy-6-alkyl-4-propinylphenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
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|---|---|---|---|---|
| US4386086A (en) * | 1978-08-24 | 1983-05-31 | Union Carbide Corporation | Method for controlling ectoparasitic Acarina |
| US4351666A (en) * | 1980-06-27 | 1982-09-28 | Union Carbide Corporation | Enol derivatives of 2-aryl-1,3-cyclohexanedione compound as sugar enhancer for plants |
| DE4004496A1 (de) * | 1990-02-14 | 1991-08-22 | Bayer Ag | 3-aryl-pyrrolidin-2,4-dion-derivate |
| AU4342096A (en) * | 1994-12-23 | 1996-07-19 | Bayer Aktiengesellschaft | 3-aryl-tetronic acid derivatives, the production thereof and the use thereof as anti-parasitic agents |
| IL146579A0 (en) * | 1999-06-16 | 2002-07-25 | Syngenta Participations Ag | Process for the preparation of herbicidal derivatives |
| PL356456A1 (en) * | 1999-09-07 | 2004-06-28 | Syngenta Participations Ag | Novel herbicides |
| RU2269537C2 (ru) * | 1999-09-07 | 2006-02-10 | Зингента Партисипейшнс Аг | Фенилзамещенные гетероциклические 1,3-кетоенолы, способ их получения, гербицидное средство на их основе и способ борьбы с ростом нежелательной растительности |
-
2003
- 2003-01-21 BR BR0306957-5A patent/BR0306957A/pt not_active Application Discontinuation
- 2003-01-21 CA CA002470674A patent/CA2470674A1/en not_active Abandoned
- 2003-01-21 JP JP2003562121A patent/JP2005516973A/ja active Pending
- 2003-01-21 US US10/502,564 patent/US20050090399A1/en not_active Abandoned
- 2003-01-21 CN CN03802204.4A patent/CN1615310A/zh active Pending
- 2003-01-21 WO PCT/EP2003/000555 patent/WO2003062244A1/en not_active Ceased
- 2003-01-21 RU RU2004125878/04A patent/RU2004125878A/ru not_active Application Discontinuation
- 2003-01-21 EP EP03702483A patent/EP1468000A1/en not_active Withdrawn
- 2003-01-21 MX MXPA04006991A patent/MXPA04006991A/es not_active Application Discontinuation
- 2003-01-21 HU HU0402592A patent/HUP0402592A2/hu unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013536818A (ja) * | 2010-09-01 | 2013-09-26 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 除草活性を有するケトスルタム類及びジケトピリジン類 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1468000A1 (en) | 2004-10-20 |
| WO2003062244A1 (en) | 2003-07-31 |
| CA2470674A1 (en) | 2003-07-31 |
| US20050090399A1 (en) | 2005-04-28 |
| CN1615310A (zh) | 2005-05-11 |
| BR0306957A (pt) | 2004-12-14 |
| HUP0402592A2 (hu) | 2005-04-28 |
| MXPA04006991A (es) | 2004-11-10 |
| RU2004125878A (ru) | 2005-05-27 |
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