JP7000160B2 - 除草剤としてのアリール置換二環式化合物 - Google Patents
除草剤としてのアリール置換二環式化合物 Download PDFInfo
- Publication number
- JP7000160B2 JP7000160B2 JP2017558947A JP2017558947A JP7000160B2 JP 7000160 B2 JP7000160 B2 JP 7000160B2 JP 2017558947 A JP2017558947 A JP 2017558947A JP 2017558947 A JP2017558947 A JP 2017558947A JP 7000160 B2 JP7000160 B2 JP 7000160B2
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- Prior art keywords
- alkyl
- cycloalkyl
- independently
- haloalkyl
- alkoxy
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 48
- 125000003118 aryl group Chemical group 0.000 title description 10
- 125000002619 bicyclic group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 309
- -1 cyano, hydroxy Chemical group 0.000 claims description 189
- 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 173
- 239000000203 mixture Substances 0.000 claims description 120
- 125000001424 substituent group Chemical group 0.000 claims description 115
- 229910052799 carbon Inorganic materials 0.000 claims description 90
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 150000001721 carbon Chemical group 0.000 claims description 63
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- 239000003112 inhibitor Substances 0.000 claims description 51
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 230000002363 herbicidal effect Effects 0.000 claims description 45
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000004122 cyclic group Chemical group 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004434 sulfur atom Chemical group 0.000 claims description 38
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 36
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 28
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 28
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 26
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 26
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 26
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 24
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 24
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 24
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 21
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 21
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 16
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 15
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 15
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 150000001204 N-oxides Chemical class 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 14
- 230000012010 growth Effects 0.000 claims description 14
- 231100000419 toxicity Toxicity 0.000 claims description 14
- 230000001988 toxicity Effects 0.000 claims description 14
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 13
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 13
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 12
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 11
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 11
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 11
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 11
- 230000000116 mitigating effect Effects 0.000 claims description 11
- 229930192334 Auxin Natural products 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- 239000002363 auxin Substances 0.000 claims description 10
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 10
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000006665 (C2 to C4) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 7
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 7
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 7
- 150000001345 alkine derivatives Chemical class 0.000 claims description 7
- 102000005396 glutamine synthetase Human genes 0.000 claims description 7
- 108020002326 glutamine synthetase Proteins 0.000 claims description 7
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 7
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 6
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 4
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- 239000005643 Pelargonic acid Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 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 3
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 3
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 3
- LYCRYYGXUAUVHL-UHFFFAOYSA-N N-(2-fluorophenyl)-6-[3-(trifluoromethyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)C1C(CN2C1=NN=C2)C1=CC(=CC=C1)C(F)(F)F LYCRYYGXUAUVHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 3
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005644 Dazomet Substances 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 2
- 230000004992 fission Effects 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 claims 2
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- 150000004668 long chain fatty acids Chemical class 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 72
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
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- 239000002904 solvent Substances 0.000 description 40
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- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-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
- 239000004550 soluble concentrate Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- LOZDOQJARMKMFN-UHFFFAOYSA-N tetraphosphorus pentasulfide Chemical compound S1P(S2)P3SP2SP1S3 LOZDOQJARMKMFN-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 group 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
- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-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
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 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
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/53—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catching Or Destruction (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/US2016/030450 WO2016182780A1 (en) | 2015-05-12 | 2016-05-02 | Aryl substituted bicyclic compounds as herbicides |
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| JP6524086B2 (ja) | 2013-12-03 | 2019-06-05 | エフ エム シー コーポレーションFmc Corporation | ピロリジノン除草剤 |
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| PL3294743T3 (pl) | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| EP3303287B1 (en) | 2015-05-29 | 2020-12-16 | FMC Corporation | Substituted cyclic amides as herbicides |
| US10654804B2 (en) | 2015-06-02 | 2020-05-19 | Fmc Corporation | Substituted cyclic amides and their use as herbicides |
| AU2016303209B2 (en) | 2015-07-31 | 2021-04-01 | Fmc Corporation | Cyclic N-carboxamide compounds useful as herbicides |
| JP2020015664A (ja) * | 2016-11-21 | 2020-01-30 | 宇部興産株式会社 | 含窒素多環式ヘテロ環誘導体 |
| EP3558962B1 (en) | 2016-12-21 | 2023-07-12 | FMC Corporation | Nitrone herbicides |
| BR112019019551A2 (pt) | 2017-03-21 | 2020-04-22 | Fmc Corp | mistura, e, método para controlar o crescimento de vegetação indesejada |
| SG11201908640TA (en) | 2017-03-21 | 2019-10-30 | Fmc Corp | Pyrrolidinones and a process to prepare them |
| WO2018177837A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | 4-cyclopentyl- und 4-cyclopropyl-2-oxopyrrolidin-3-carboxami d-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| WO2018177836A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | N-cyclopropyl-2-oxopyrrolidin-3-carboxamid-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| WO2019025156A1 (de) | 2017-08-03 | 2019-02-07 | Bayer Aktiengesellschaft | Substituierte pyrrolidinone sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2020064260A1 (de) | 2018-09-24 | 2020-04-02 | Bayer Aktiengesellschaft | Substituierte 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamide sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| JP2022106302A (ja) * | 2019-05-30 | 2022-07-20 | 石原産業株式会社 | 除草組成物 |
| CN112844856B (zh) * | 2020-12-21 | 2021-11-26 | 中南大学 | 一种萤石和脉石浮选分离的复合抑制剂、复合浮选药剂和方法 |
| IL313538A (en) | 2021-12-15 | 2024-08-01 | Adama Agan Ltd | Useful compounds for the preparation of various agrochemicals and their markers |
| KR20250160506A (ko) * | 2023-03-23 | 2025-11-13 | 에프엠씨 코포레이션 | 제초제로서의 치환된 옥사졸리디논 및 이미다졸리논 |
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