JP7184813B2 - 除草用アミド - Google Patents
除草用アミド Download PDFInfo
- Publication number
- JP7184813B2 JP7184813B2 JP2019566131A JP2019566131A JP7184813B2 JP 7184813 B2 JP7184813 B2 JP 7184813B2 JP 2019566131 A JP2019566131 A JP 2019566131A JP 2019566131 A JP2019566131 A JP 2019566131A JP 7184813 B2 JP7184813 B2 JP 7184813B2
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- JP
- Japan
- Prior art keywords
- ring
- alkyl
- independently selected
- compound
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000002363 herbicidal effect Effects 0.000 title claims description 35
- 150000001408 amides Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 273
- -1 cyano, hydroxy Chemical group 0.000 claims description 166
- 125000001424 substituent group Chemical group 0.000 claims description 107
- 239000000203 mixture Substances 0.000 claims description 96
- 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 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 229910052799 carbon Inorganic materials 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 150000002367 halogens Chemical group 0.000 claims description 65
- 125000004122 cyclic group Chemical group 0.000 claims description 57
- 239000003112 inhibitor Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
- 239000004009 herbicide Substances 0.000 claims description 39
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 35
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 239000007787 solid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 26
- 150000001721 carbon Chemical group 0.000 claims description 26
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 20
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 15
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 14
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 14
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 14
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 14
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 13
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims description 12
- 229930192334 Auxin Natural products 0.000 claims description 12
- 239000002363 auxin Substances 0.000 claims description 12
- 230000012010 growth Effects 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 8
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 8
- 108010018763 Biotin carboxylase Proteins 0.000 claims description 8
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 8
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 8
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 7
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 7
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 7
- 108030006708 Homogentisate solanesyltransferases Proteins 0.000 claims description 7
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 7
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 7
- 102000005396 glutamine synthetase Human genes 0.000 claims description 7
- 108020002326 glutamine synthetase Proteins 0.000 claims description 7
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 7
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 7
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 5
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 5
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- JIDAHYHCQJXNTD-UHFFFAOYSA-N 4-(hydrazinecarbonyl)benzenesulfonamide Chemical compound NNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 JIDAHYHCQJXNTD-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005643 Pelargonic acid Substances 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 3
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 2
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- 238000009472 formulation Methods 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- 125000000623 heterocyclic group Chemical group 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 150000002148 esters Chemical group 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000003871 sulfonates Chemical class 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 5
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- 238000012545 processing Methods 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
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- 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
- 238000007348 radical reaction Methods 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- 239000005871 repellent Substances 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
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- 235000005713 safflower oil Nutrition 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
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- 238000004062 sedimentation Methods 0.000 description 1
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- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
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- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762512683P | 2017-05-30 | 2017-05-30 | |
| US62/512,683 | 2017-05-30 | ||
| PCT/US2018/035015 WO2018222646A1 (en) | 2017-05-30 | 2018-05-30 | Herbicidal amides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020522493A JP2020522493A (ja) | 2020-07-30 |
| JP2020522493A5 JP2020522493A5 (enExample) | 2021-07-26 |
| JP7184813B2 true JP7184813B2 (ja) | 2022-12-06 |
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|---|---|---|---|
| JP2019566131A Active JP7184813B2 (ja) | 2017-05-30 | 2018-05-30 | 除草用アミド |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11357230B2 (enExample) |
| EP (1) | EP3630721B1 (enExample) |
| JP (1) | JP7184813B2 (enExample) |
| CN (1) | CN110944977A (enExample) |
| AR (1) | AR111967A1 (enExample) |
| AU (1) | AU2018277537B2 (enExample) |
| BR (1) | BR112019024988B1 (enExample) |
| CA (1) | CA3064578A1 (enExample) |
| RU (1) | RU2019143102A (enExample) |
| WO (1) | WO2018222646A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| JP7000160B2 (ja) | 2015-05-12 | 2022-01-19 | エフ エム シー コーポレーション | 除草剤としてのアリール置換二環式化合物 |
| US10654804B2 (en) | 2015-06-02 | 2020-05-19 | Fmc Corporation | Substituted cyclic amides and their use as herbicides |
| AU2017378640B2 (en) | 2016-12-21 | 2022-03-03 | Fmc Corporation | Nitrone herbicides |
| MX2019011090A (es) | 2017-03-21 | 2019-11-18 | Fmc Corp | Mezcla herbicida, composición y método. |
| US10875838B2 (en) | 2017-03-21 | 2020-12-29 | Fmc Corporation | Pyrrolidinones and a process to prepare them |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| EP4447681A2 (en) | 2021-12-15 | 2024-10-23 | Adama Agan Ltd. | Compounds useful for the preparation of various agrochemicals and markers thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016003997A1 (en) | 2014-07-02 | 2016-01-07 | E. I. Du Pont De Nemours And Company | Piperidinone herbicides |
| WO2016164201A1 (en) | 2015-04-10 | 2016-10-13 | E I Du Pont De Nemours And Company | Substituted cyclic amides as herbicides |
| WO2016196019A1 (en) | 2015-05-29 | 2016-12-08 | E I Du Pont De Nemours And Company | Substituted cyclic amides as herbicides |
| WO2016196593A1 (en) | 2015-06-02 | 2016-12-08 | E I Du Pont De Nemours And Company | Substituted cyclic amides and their use as herbicides |
| JP2017506210A (ja) | 2013-12-03 | 2017-03-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | ピロリジノン除草剤 |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| DE1262277B (de) | 1962-12-05 | 1968-03-07 | Basf Ag | Verfahren zur Herstellung von Pyrrolidonen |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
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- 2018-05-30 JP JP2019566131A patent/JP7184813B2/ja active Active
- 2018-05-30 US US16/614,870 patent/US11357230B2/en active Active
- 2018-05-30 RU RU2019143102A patent/RU2019143102A/ru unknown
- 2018-05-30 CN CN201880049311.3A patent/CN110944977A/zh active Pending
- 2018-05-30 BR BR112019024988-5A patent/BR112019024988B1/pt not_active IP Right Cessation
- 2018-05-30 WO PCT/US2018/035015 patent/WO2018222646A1/en not_active Ceased
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| BR112019024988A2 (pt) | 2020-06-16 |
| US11357230B2 (en) | 2022-06-14 |
| AU2018277537A1 (en) | 2019-11-28 |
| EP3630721B1 (en) | 2022-01-05 |
| EP3630721A1 (en) | 2020-04-08 |
| RU2019143102A (ru) | 2021-06-30 |
| CA3064578A1 (en) | 2018-12-06 |
| JP2020522493A (ja) | 2020-07-30 |
| AU2018277537B2 (en) | 2022-04-14 |
| BR112019024988B1 (pt) | 2023-12-26 |
| WO2018222646A1 (en) | 2018-12-06 |
| US20200154709A1 (en) | 2020-05-21 |
| CN110944977A (zh) | 2020-03-31 |
| AR111967A1 (es) | 2019-09-04 |
| RU2019143102A3 (enExample) | 2021-10-01 |
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