AU749237B2 - Substituted benzene compounds, process for their preparation, and herbicidal and defolient compositions containing them - Google Patents
Substituted benzene compounds, process for their preparation, and herbicidal and defolient compositions containing them Download PDFInfo
- Publication number
- AU749237B2 AU749237B2 AU95650/98A AU9565098A AU749237B2 AU 749237 B2 AU749237 B2 AU 749237B2 AU 95650/98 A AU95650/98 A AU 95650/98A AU 9565098 A AU9565098 A AU 9565098A AU 749237 B2 AU749237 B2 AU 749237B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- amino
- aryl
- halogen
- alkoxycarbonyl
- 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.)
- Ceased
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- 239000000203 mixture Substances 0.000 title claims description 96
- 238000000034 method Methods 0.000 title claims description 55
- 230000002363 herbicidal effect Effects 0.000 title claims description 48
- 230000008569 process Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 90
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- -1 nitro, amino Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000000304 alkynyl group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 241000196324 Embryophyta Species 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 23
- 238000009472 formulation Methods 0.000 claims description 23
- 239000004009 herbicide Substances 0.000 claims description 23
- 238000012360 testing method Methods 0.000 claims description 23
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 12
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- TZOJTTXGUGCIMN-UHFFFAOYSA-N 3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C(Cl)C(OC)=C(N)C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F TZOJTTXGUGCIMN-UHFFFAOYSA-N 0.000 claims description 9
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 8
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims 1
- 244000061456 Solanum tuberosum Species 0.000 claims 1
- 150000003934 aromatic aldehydes Chemical class 0.000 claims 1
- 150000008365 aromatic ketones Chemical class 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 239000000460 chlorine Substances 0.000 description 123
- 239000000243 solution Substances 0.000 description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 50
- 239000002904 solvent Substances 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
- 239000000741 silica gel Substances 0.000 description 44
- 229910002027 silica gel Inorganic materials 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 39
- 239000004480 active ingredient Substances 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 230000002829 reductive effect Effects 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 28
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 25
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 25
- 229910017604 nitric acid Inorganic materials 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 229940086542 triethylamine Drugs 0.000 description 19
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001989 diazonium salts Chemical class 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 8
- 238000006396 nitration reaction Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- HBGYPLNIBDKWIK-UHFFFAOYSA-N 1-chloro-2,5-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=C(Cl)C=C1F HBGYPLNIBDKWIK-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PYRVOUSDQGBZRG-UHFFFAOYSA-N 4-chloro-2,5-difluoroaniline Chemical compound NC1=CC(F)=C(Cl)C=C1F PYRVOUSDQGBZRG-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000010531 catalytic reduction reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 241000894007 species Species 0.000 description 6
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 238000001212 derivatisation Methods 0.000 description 5
- AHQUDOBVJYZXQJ-UHFFFAOYSA-N ethyl n-(4-chloro-2,5-difluorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC(F)=C(Cl)C=C1F AHQUDOBVJYZXQJ-UHFFFAOYSA-N 0.000 description 5
- MWBUQEJNTZWZKW-UHFFFAOYSA-N ethyl n-(4-chloro-3,6-difluoro-2-nitrophenyl)carbamate Chemical compound CCOC(=O)NC1=C(F)C=C(Cl)C(F)=C1[N+]([O-])=O MWBUQEJNTZWZKW-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 150000008512 pyrimidinediones Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000004546 suspension concentrate Substances 0.000 description 5
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 5
- QZBAYURFHCTXOJ-OWOJBTEDSA-M (e)-4,4,4-trifluorobut-2-enoate Chemical compound [O-]C(=O)\C=C\C(F)(F)F QZBAYURFHCTXOJ-OWOJBTEDSA-M 0.000 description 4
- ZFFFGWHDGIYGCK-UHFFFAOYSA-N 2-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-(trifluoromethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(OC)=C(N)C(N2C(C=C(C=N2)C(F)(F)F)=O)=C1F ZFFFGWHDGIYGCK-UHFFFAOYSA-N 0.000 description 4
- 240000006995 Abutilon theophrasti Species 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- 244000237956 Amaranthus retroflexus Species 0.000 description 4
- 244000277285 Cassia obtusifolia Species 0.000 description 4
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 244000067505 Xanthium strumarium Species 0.000 description 4
- NVVGMIRCFUVBOB-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O NVVGMIRCFUVBOB-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- UUIMWAYSWRNKBM-UHFFFAOYSA-N n-[3-chloro-2-(difluoromethoxy)-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]naphthalene-2-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(F)C=C(Cl)C(OC(F)F)=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1 UUIMWAYSWRNKBM-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IHXCTUUEAODLKC-UHFFFAOYSA-N n-[5-chloro-2-(1,3-dioxoisoindol-2-yl)phenyl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NC=3C(N4C(C5=CC=CC=C5C4=O)=O)=CC=C(C=3)Cl)=CC=C21 IHXCTUUEAODLKC-UHFFFAOYSA-N 0.000 description 1
- JKNOGNFVBSRCLY-UHFFFAOYSA-N n-[5-chloro-3-fluoro-2-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]naphthalene-2-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(F)C=C(Cl)C=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1 JKNOGNFVBSRCLY-UHFFFAOYSA-N 0.000 description 1
- VHEWQRWLIDWRMR-UHFFFAOYSA-N n-[methoxy-(4-methyl-2-nitrophenoxy)phosphinothioyl]propan-2-amine Chemical compound CC(C)NP(=S)(OC)OC1=CC=C(C)C=C1[N+]([O-])=O VHEWQRWLIDWRMR-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 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
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000011368 organic material Substances 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
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000010816 packaging waste Substances 0.000 description 1
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000035515 penetration Effects 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
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 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
- IXZNVMPQRBJDEJ-UHFFFAOYSA-N phenyl n-(4-chloro-2-fluoro-5-methylphenyl)carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC=2C=CC=CC=2)=C1F IXZNVMPQRBJDEJ-UHFFFAOYSA-N 0.000 description 1
- GPUJIUUGYUTSOO-UHFFFAOYSA-N phenyl n-[3-chloro-5-fluoro-2-methyl-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]carbamate Chemical compound CC1=C(Cl)C=C(F)C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1NC(=O)OC1=CC=CC=C1 GPUJIUUGYUTSOO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
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- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-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
- IKVXBIIHQGXQRQ-CYBMUJFWSA-N propan-2-yl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-CYBMUJFWSA-N 0.000 description 1
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- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 238000001243 protein synthesis Methods 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
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- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 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
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 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
- 238000007363 ring formation reaction Methods 0.000 description 1
- 102200014835 rs727505186 Human genes 0.000 description 1
- 235000009165 saligot Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 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
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 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
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 230000014616 translation Effects 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
- 125000005310 triazolidinyl group Chemical class N1(NNCC1)* 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
- 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
- 150000003672 ureas Chemical class 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N37/34—Nitriles
-
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- 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
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- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| PCT/US1998/017197 WO1999021837A1 (en) | 1997-10-27 | 1998-08-21 | Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them |
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| AU95650/98A Ceased AU749237B2 (en) | 1997-10-27 | 1998-08-21 | Substituted benzene compounds, process for their preparation, and herbicidal and defolient compositions containing them |
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| DE19520613A1 (de) | 1995-06-06 | 1996-12-12 | Bayer Ag | Phenylpyridazinone |
| DE19708928A1 (de) * | 1997-03-05 | 1998-09-10 | Bayer Ag | Substituierte aromatische Aminoverbindungen |
| EP1014962A4 (en) * | 1997-06-26 | 2007-06-27 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
| JP2001072668A (ja) | 1999-07-07 | 2001-03-21 | Sumitomo Chem Co Ltd | ウラシル化合物およびその用途 |
| UA76708C2 (uk) * | 1999-12-08 | 2006-09-15 | Сінгента Патисипейшонс Аг | Антитіло, яке застосовується в імунологічному аналізі зразка для визначення неонікотиноїдного інсектициду, білковий кон'югат для одержання антитіла, спосіб визначення концентрації неонікотиноїдного інсектициду в зразку та набір для визначення кількості неонікотиноїдного інсектициду |
| DE10016893A1 (de) | 2000-04-05 | 2001-10-18 | Bayer Ag | Substituierte Phenyluracile |
| EP1178035B1 (en) * | 2000-08-04 | 2008-07-30 | Bayer CropScience S.A. | Fungicidal phenylimine derivatives |
| EP1180512A1 (en) | 2000-08-04 | 2002-02-20 | Aventis Cropscience S.A. | Fungicidal phenylimine derivatives |
| US8232230B2 (en) * | 2000-12-01 | 2012-07-31 | Helena Holding Company | Manufacture and use of a herbicide formulation |
| ATE380172T1 (de) | 2001-01-26 | 2007-12-15 | Btg Int Ltd | Benzylaminanalogen |
| US6613718B2 (en) * | 2001-10-01 | 2003-09-02 | Ishihara Sangyo Kaisha, Ltd. | Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them |
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| ATE325115T1 (de) * | 2002-08-19 | 2006-06-15 | Glaxo Group Ltd | Pyrimidinderivate als selektive cox-2-inhibitoren |
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| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| US7429603B2 (en) * | 2003-04-25 | 2008-09-30 | 3-Dimensional Pharmaceuticals, Inc. | C-fms kinase inhibitors |
| US7427683B2 (en) * | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| US7790724B2 (en) * | 2003-04-25 | 2010-09-07 | Janssen Pharmaceutica N.V. | c-fms kinase inhibitors |
| ES2524922T3 (es) | 2005-05-10 | 2014-12-15 | Intermune, Inc. | Derivados de piridona para modular el sistema de proteína cinasa activada por estrés |
| US8426341B2 (en) * | 2005-05-27 | 2013-04-23 | Helena Holding Company | Herbicide formulation |
| CA2672494A1 (en) * | 2006-12-14 | 2008-06-19 | Nps Pharmaceuticals, Inc. | Use of d-serine derivatives for the treatment of anxiety disorders |
| CA2726588C (en) | 2008-06-03 | 2019-04-16 | Karl Kossen | Compounds and methods for treating inflammatory and fibrotic disorders |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| SG11201509186TA (en) * | 2013-06-27 | 2016-01-28 | Pfizer | Heteroaromatic compounds and their use as dopamine d1 ligands |
| US10091998B2 (en) | 2013-10-28 | 2018-10-09 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and use thereof |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
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-
1998
- 1998-08-21 EP EP98949302A patent/EP1030843A4/en not_active Withdrawn
- 1998-08-21 CN CNA2005100628986A patent/CN1673219A/zh active Pending
- 1998-08-21 BR BR9814104-0A patent/BR9814104A/pt not_active Application Discontinuation
- 1998-08-21 CN CN98812711A patent/CN1283190A/zh active Pending
- 1998-08-21 CN CNA2005100652716A patent/CN1680274A/zh active Pending
- 1998-08-21 JP JP2000517949A patent/JP2001521027A/ja active Pending
- 1998-08-21 HU HU0004151A patent/HUP0004151A3/hu not_active Application Discontinuation
- 1998-08-21 WO PCT/US1998/017197 patent/WO1999021837A1/en not_active Ceased
- 1998-08-21 US US09/530,373 patent/US6355799B1/en not_active Ceased
- 1998-08-21 AU AU95650/98A patent/AU749237B2/en not_active Ceased
- 1998-08-21 CA CA002307815A patent/CA2307815A1/en not_active Abandoned
- 1998-10-22 PE PE1998000999A patent/PE131399A1/es not_active Application Discontinuation
- 1998-10-22 ZA ZA989639A patent/ZA989639B/xx unknown
- 1998-10-23 TW TW087117635A patent/TW533200B/zh not_active IP Right Cessation
- 1998-10-26 CO CO98062198A patent/CO5090848A1/es unknown
- 1998-10-26 HN HN1998000166A patent/HN1998000166A/es unknown
- 1998-10-26 AR ARP980105337A patent/AR014384A1/es unknown
- 1998-10-27 PA PA19988462201A patent/PA8462201A1/es unknown
- 1998-10-27 EG EG130998A patent/EG22047A/xx active
- 1998-10-27 MY MYPI98004882A patent/MY136948A/en unknown
- 1998-10-27 UY UY25224A patent/UY25224A1/es not_active IP Right Cessation
- 1998-10-27 GT GT199800164A patent/GT199800164A/es unknown
-
2000
- 2000-04-27 US US10/797,936 patent/USRE39590E1/en not_active Expired - Fee Related
-
2001
- 2001-08-16 US US09/930,149 patent/US6545161B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6355799B1 (en) | 2002-03-12 |
| CN1283190A (zh) | 2001-02-07 |
| CN1680274A (zh) | 2005-10-12 |
| JP2001521027A (ja) | 2001-11-06 |
| CO5090848A1 (es) | 2001-10-30 |
| USRE39590E1 (en) | 2007-04-24 |
| WO1999021837A1 (en) | 1999-05-06 |
| EP1030843A4 (en) | 2002-11-06 |
| MY136948A (en) | 2008-12-31 |
| BR9814104A (pt) | 2001-12-26 |
| ZA989639B (en) | 1999-04-26 |
| HN1998000166A (es) | 1999-01-08 |
| AU9565098A (en) | 1999-05-17 |
| HUP0004151A2 (hu) | 2001-02-28 |
| EP1030843A1 (en) | 2000-08-30 |
| US20020133007A1 (en) | 2002-09-19 |
| CA2307815A1 (en) | 1999-05-06 |
| CN1673219A (zh) | 2005-09-28 |
| PA8462201A1 (es) | 2001-07-31 |
| UY25224A1 (es) | 2001-01-31 |
| PE131399A1 (es) | 2000-01-25 |
| HUP0004151A3 (en) | 2001-12-28 |
| GT199800164A (es) | 2000-04-19 |
| TW533200B (en) | 2003-05-21 |
| AR014384A1 (es) | 2001-02-28 |
| US6545161B2 (en) | 2003-04-08 |
| EG22047A (en) | 2002-06-30 |
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