CN1220663A - 取代的苯基尿嘧啶 - Google Patents
取代的苯基尿嘧啶 Download PDFInfo
- Publication number
- CN1220663A CN1220663A CN97195075A CN97195075A CN1220663A CN 1220663 A CN1220663 A CN 1220663A CN 97195075 A CN97195075 A CN 97195075A CN 97195075 A CN97195075 A CN 97195075A CN 1220663 A CN1220663 A CN 1220663A
- Authority
- CN
- China
- Prior art keywords
- amino
- group
- optional
- alkyl
- phenyl
- 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.)
- Granted
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 20
- -1 thiocarbamoyl Chemical group 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005864 Sulphur Substances 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- TWBIDQDUOXHFSN-UHFFFAOYSA-N C[CH]C=O Chemical compound C[CH]C=O TWBIDQDUOXHFSN-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 abstract 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000003999 initiator Substances 0.000 description 15
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 241000219318 Amaranthus Species 0.000 description 6
- 241000207763 Solanum Species 0.000 description 6
- 235000002634 Solanum Nutrition 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000219144 Abutilon Species 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- 241000219312 Chenopodium Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 244000192528 Chrysanthemum parthenium Species 0.000 description 4
- 241000208296 Datura Species 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 235000017945 Matricaria Nutrition 0.000 description 4
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000209117 Panicum Species 0.000 description 4
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
- 241000205407 Polygonum Species 0.000 description 4
- 235000005775 Setaria Nutrition 0.000 description 4
- 241000232088 Setaria <nematode> Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 241000209072 Sorghum Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 241001506766 Xanthium Species 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- 229960000278 theophylline Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 241000801118 Lepidium Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 229960003280 cupric chloride Drugs 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000209136 Agropyron Species 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 241000404028 Anthemis Species 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 241000611157 Brachiaria Species 0.000 description 2
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 2
- 244000098897 Chenopodium botrys Species 0.000 description 2
- 235000005490 Chenopodium botrys Nutrition 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 2
- 244000024469 Cucumis prophetarum Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 241000208175 Daucus Species 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 241000202829 Eleocharis Species 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- 241001290564 Fimbristylis Species 0.000 description 2
- 241001101998 Galium Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 235000009438 Gossypium Nutrition 0.000 description 2
- 241000209219 Hordeum Species 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241000208204 Linum Species 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000011096 Papaver Nutrition 0.000 description 2
- 240000001090 Papaver somniferum Species 0.000 description 2
- 241000219833 Phaseolus Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000219843 Pisum Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 241000219295 Portulaca Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000218206 Ranunculus Species 0.000 description 2
- 241000209056 Secale Species 0.000 description 2
- 241000780602 Senecio Species 0.000 description 2
- 244000275012 Sesbania cannabina Species 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000488874 Sonchus Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 241000219422 Urtica Species 0.000 description 2
- 241000219873 Vicia Species 0.000 description 2
- 241000405217 Viola <butterfly> Species 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 244000193174 agave Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 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 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 1
- QQOGZMUZAZWLJH-UHFFFAOYSA-N 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-n-ethylsulfonyl-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)CC)=CC(OC=2C(=CC(=CC=2F)C(F)(F)F)Cl)=C1 QQOGZMUZAZWLJH-UHFFFAOYSA-N 0.000 description 1
- KNCHDRLWPAKSII-UHFFFAOYSA-N 5-ethyl-2-methylpyridine Natural products CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- HJIYHOVBJRVELV-UHFFFAOYSA-N C(C)OCC(=S)OCCO Chemical compound C(C)OCC(=S)OCCO HJIYHOVBJRVELV-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000320316 Carduus Species 0.000 description 1
- 244000036828 Carduus nutans Species 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- IKYQZFPRVFNIPU-UHFFFAOYSA-N ClNC1=CC=C(C=C1)C(C)=O Chemical class ClNC1=CC=C(C=C1)C(C)=O IKYQZFPRVFNIPU-UHFFFAOYSA-N 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 239000005499 Clomazone Substances 0.000 description 1
- 239000005500 Clopyralid Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000019093 Cucurbita foetidissima Nutrition 0.000 description 1
- 244000149213 Cucurbita foetidissima Species 0.000 description 1
- 241000320605 Dactyloctenium Species 0.000 description 1
- 239000005503 Desmedipham Substances 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 239000005507 Diflufenican Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- 235000006369 Emex spinosa Nutrition 0.000 description 1
- 244000294661 Emex spinosa Species 0.000 description 1
- 241001517310 Eria Species 0.000 description 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000005512 Ethofumesate Substances 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- 239000005558 Fluroxypyr Substances 0.000 description 1
- 241000816457 Galeopsis Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 241001138408 Glyptostrobus pensilis Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 239000005570 Isoxaben Substances 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000064140 Lindernia Species 0.000 description 1
- 235000002262 Lycopersicon Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
- 239000005579 Metamitron Substances 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241001504654 Mustela nivalis Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VQWWKYLNRCKQRP-UHFFFAOYSA-N N[Ca] Chemical compound N[Ca] VQWWKYLNRCKQRP-UHFFFAOYSA-N 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000005587 Oryzalin Substances 0.000 description 1
- 239000005590 Oxyfluorfen Substances 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 241001330453 Paspalum Species 0.000 description 1
- 241001268782 Paspalum dilatatum Species 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- 241001092090 Pittosporum Species 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000005603 Prosulfocarb Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- 239000005606 Pyridate Substances 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- 241000490453 Rorippa Species 0.000 description 1
- 241000341978 Rotala Species 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 235000017967 Sphenoclea zeylanica Nutrition 0.000 description 1
- 244000273618 Sphenoclea zeylanica Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000245665 Taraxacum Species 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- 239000005625 Tri-allate Substances 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- 239000005627 Triclopyr Substances 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- 241000159750 Urtica cannabina Species 0.000 description 1
- 241001573053 Vandellia Species 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- FDTAOSBGUZWNSN-UHFFFAOYSA-N [Cl].[F].N1C=CC=C1 Chemical compound [Cl].[F].N1C=CC=C1 FDTAOSBGUZWNSN-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- REEJOFMTJPOBAY-UHFFFAOYSA-N benzene;1h-pyrrole Chemical class C=1C=CNC=1.C1=CC=CC=C1 REEJOFMTJPOBAY-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- SILSDTWXNBZOGF-KUZBFYBWSA-N chembl111058 Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N\OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-KUZBFYBWSA-N 0.000 description 1
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 1
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical class CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical class O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-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
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012875 nonionic emulsifier Substances 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
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000011146 organic particle 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
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-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
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 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
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-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
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 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
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及通式(Ⅰ)新的取代的苯基尿嘧啶,其中R1代表氢,卤素或任选被取代的烷基,R2代表任选被取代的烷基,R3代表氢,氨基或者代表烷基,链烯基或炔烃基,其各自任选被取代,R4代表氢,氰基或卤素,R5代表氰基或硫代氨基甲酰基,和R6代表下面式的基团之一,其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或任选被取代的烷基,R8代表氢,羟基,氨基或者代表烷基,烷氧基,烷基氨基,二烷基氨基,烷基羰基氨基,烷基磺酰基氨基,链烯基,链烯基氧基,炔烃基,环烷基,环烷基氧基,环烷基氨基,环烷基羰基氨基,环烷基磺酰基氨基,芳基,芳基氧基,芳基氨基,芳基羰基氨基,芳基磺酰基氨基,芳基烷基,芳基烷氧基,芳基烷基氨基,其中各基团任选被取代,和R9和R10各自代表烷基,并且涉及其制备方法,以及涉及其作为除草剂的用途。
Description
本发明涉及新的取代的苯基尿嘧啶,其制备方法,以及其作为除草剂的用途。
已知一些取代的尿嘧啶具有除草性质(参见DE 4131038,DE4237920,DE4329537,EP 408382/US 5084084/US 5127935/US 5154755,EP 542685,EP 563384,EP 648749,US 4979982,US 5169430,WO91/00278,WO 95/25725)。但是,迄今为止这些化合物还没有获得任何重要的有价值的陈述。
因此,本发明提供通式(Ⅰ)新的取代的苯基尿嘧啶:其中R1代表氢,卤素或任选被取代的烷基,R2代表任选被取代的烷基,R3代表氢,氨基或者代表烷基,链烯基或炔烃基,其各自任选被取代,R4代表氢,氰基或卤素,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或任选被取代的烷基,R8代表氢,羟基,氨基或者代表烷基,烷氧基,烷基氨基,二烷基氨基,烷基羰基氨基,烷基磺酰基氨基,链烯基,链烯基氧基,炔烃基,环烷基,环烷基氧基,环烷基氨基,环烷基羰基氨基,环烷基磺酰基氨基,芳基,芳基氧基,芳基氨基,芳基羰基氨基,芳基磺酰基氨基,芳基烷基,芳基烷氧基,芳基烷基氨基,其中各基团任选被取代,并且R9和R10各自代表烷基。
当进行下面的反应时得到了通式(Ⅰ)新的取代的苯基尿嘧啶:(a)如果适当在稀释剂存在下和如果适当在反应助剂存在下,通式(Ⅱ)的链烯基苯基尿嘧啶与臭氧反应,其中R1,R2,R3,R4,R5和R7各自如上定义,和R11和R12各自代表氢,氰基,羧基或者代表各自任选被取代的烷基或烷氧羰基,或者(b)如果适当在稀释剂存在下和如果适当在反应助剂存在下,通式(Ⅰa)羰基苯基尿嘧啶与通式(Ⅲ)氨基化合物,或与式(Ⅲ)化合物的酸加成物反应,其中R1,R2,R3,R4,R5和R7各自如上定义,
H2N-R8 (Ⅲ)其中R8如上定义,或者(c)如果适当在稀释剂存在下和如果适当在反应助剂存在下,通式(Ⅰa)羰基苯基尿嘧啶与通式(Ⅳa)或(Ⅳb)醇和/或硫醇反应,其中R1,R2,R3,R4,R5和R7各自如上定义,
HQ1R9 (Ⅳa) HQ2R10 (Ⅳb)其中Q1,Q2,R9和R10各自如上定义。
通式(Ⅰ)化合物也可以根据上述定义应用其它常规方法转化成其它通式(Ⅰ)化合物,例如通过胺化作用和/或烷基化作用(例如R3:H→NH2,H→CH3),通过与硫化氢反应(例如R5:CN→CSNH2)。
通式(Ⅰ)新的取代的苯基尿嘧啶具有强的除草活性。
在上述定义中,饱和的或不饱和的烃链,例如烷基,链烯基或炔烃基在每种情况下是直链或支链的。
卤素一般代表氟,氯,溴或碘,优选代表氟,氯或溴,特别代表氟或氯。
本发明优选提供下列式(Ⅰ)化合物,其中R1代表氢,氟,氯,溴或任选被氟-和/或氯-取代的C1-C4-烷基,R2代表任选被氟-和/或氯-取代的C1-C4-烷基,R3代表氢,氨基,代表任选被氰基-,氟-,氯-或C1-C4-烷氧基-取代的C1-C6-烷基,或者代表任选被氟-和/或氯-取代的C2-C6-链烯基或C2-C6-炔烃基,R4代表氢,氰基,氟或氯,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或代表任选被卤素-或C1-C4-烷氧基-取代的C1-C4-烷基,R8代表氢,羟基,氨基,代表C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷基氨基,二-(C1-C4-烷基)-氨基,C1-C4-烷基羰基氨基或C1-C4-烷基磺酰基氨基,其中各基团任选被卤素,C1-C4-烷氧基或C1-C4-烷氧羰基取代,代表C2-C6-链烯基,C2-C6-链烯基氧基,C2-C6-炔烃基,其中各基团任选被卤素取代,代表C3-C6-环烷基,C3-C6-环烷基氧基,C3-C6-环烷基氨基,C3-C6-环烷基羰基氨基或C3-C6-环烷基磺酰基氨基,其中各基团任选被卤素或C1-C4-烷基取代,或者代表苯基,苯氧基,苯基氨基,苯基羰基氨基,苯基磺酰基氨基,苯基-C1-C4-烷基,苯基-C1-C4-烷氧基,苯基-C1-C4-烷基氨基,其中各基团任选被卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基取代,并且R9和R10各自代表C1-C4-烷基。
本发明特别涉及下列式(Ⅰ)化合物,其中R1代表氢,氟,氯,溴或任选被氟-和/或氯-取代的甲基或乙基,R2代表任选被氟-和/或氯-取代的甲基或乙基,R3代表氢,氨基,代表各自任选被氰基-,氟-,氯-,甲氧基或乙氧基取代的甲基,乙基,正-,或异-,丙基,正-,异-,仲或叔-丁基,或者代表任选被氟-和/或氯-取代的丙烯基,丁烯基,丙炔基或丁炔基,R4代表氢,氟或氯,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基或乙基,R8代表氢,羟基,氨基,代表甲基,乙基,正-或异-丙基,正-、异-、仲或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,正-、异-、仲或叔-丁氧基,甲基氨基,乙基氨基,正-或异-丙基氨基,正-、异-、仲或叔-丁基氨基,二甲基氨基,乙酰基氨基,丙酰基氨基,正-或异-丁酰基氨基,甲基磺酰基氨基或乙基磺酰基氨基,其中各基团任选被氟,氯,甲氧基,乙氧基,甲氧羰基或乙氧羰基取代,代表丙烯基,丁烯基,丙烯基氧基,丁烯基氧基,丙炔基或丁炔基,其中各基团任选被氟,氯或溴取代,代表环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基,环丙基羰基氨基,环丁基羰基氨基,环戊基羰基氨基,环己基羰基氨基,环丙基磺酰基氨基,环丁基磺酰基氨基,环戊基磺酰基氨基或环己基磺酰基氨基,其中各基团任选被氟,氯,溴,甲基或乙基取代,或者代表苯基,苯基氨基,苯基羰基氨基,苯基磺酰基氨基,苄基,苄基氧基或苄基氨基,其中各基团任选被氟,氯,溴,甲基,乙基,三氟甲基,甲氧基,乙氧基,二氟甲氧基或三氟甲氧基取代,和R9和R10各自代表甲基或乙基。
上述一般或优选的基团的定义适用于式(Ⅰ)终产物和相应适用于用于制备的各种情况下需要的起始物或中间体。这些基团的定义可以根据需要相互组合,即包括指出的优选的范围之间的组合。
根据本发明的式(Ⅰ)化合物的实例在下面的组中列出。
第1组
R6在这种情况下具有例如下面给出的定义:
甲酰基,乙酰基,甲基亚氨基甲基,乙基亚氨基乙基,正丙基亚氨基甲基,异丙基亚氨基甲基,肟基甲基,甲氧亚氨基甲基,乙氧亚氨基甲基,正丙氧亚氨基甲基,异丙氧亚氨基甲基,正丁氧亚氨基甲基,1-甲氧亚氨基-乙基,甲氧羰基甲氧亚氨基甲基,乙氧羰基甲氧亚氨基甲基,1-甲氧羰基甲氧亚氨基-乙基,1-乙氧羰基甲氧亚氨基-乙基,1,2-亚肼代亚氨基甲基,甲基1,2-亚肼代亚氨基甲基,二甲基1,2-亚肼代亚氨基甲基,乙酰基1,2-亚肼代亚氨基甲基,甲基磺酰基1,2-亚肼代亚氨基甲基,烯丙氧亚氨基甲基,环戊基氧亚氨基甲基,环己基氧亚氨基甲基,苄基氧亚氨基甲基,环戊基1,2-亚肼代亚氨基甲基,环己基1,2-亚肼代亚氨基甲基,苯基1,2-亚肼代亚氨基甲基,苯基羰基1,2-亚肼代亚氨基甲基,苯基磺酰基1,2-亚肼代亚氨基甲基,苄基1,2-亚肼代亚氨基甲基,二甲氧基甲基,二乙氧基甲基。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。。
第7组
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
第14组
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
R6在这种情况下具有例如上面第1组中给出的意义。
使用例如1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和臭氧为起始物,则本发明方法(a)的反应过程可以通过下面的反应式来说明:使用例如1-[4-氰基-2-氟-5-甲酰基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和O-甲基-羟基胺为起始物,则本发明方法(b)的反应过程可以通过下面的反应式来说明:
使用例如1-[4-氰基-2-氟-5-甲酰基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和甲醇为起始物,则本发明方法(c)的反应过程可以通过下面的反应式来说明:
式(Ⅱ)提供了为了制备通式(Ⅰ)的化合物而在本发明方法(a)中用作起始物的链烯基苯基尿嘧啶的通式定义。在式(Ⅱ)中,R1,R2,R3,R4,R5和R7各自优选地或特别地具有上文已经指出的,与说明根据本发明制备的式(Ⅰ)化合物相关的,作为优选的或特别优选的R1,R2,R3,R4,R5和R7的定义;R11和R12优选代表氰基,羧基或C1-C4-烷氧羰基。
式(Ⅱ)起始物迄今为止还未在文献中公开;作为新的物质,其构成先前技术但是没有预先公开的申请(参见DE 19528186)的一个主题。
如果适当在稀释剂存在下,例如在水,乙酸,乙腈和二氯甲烷的存在下,在-20℃和+10℃之间的温度下,当通式(Ⅴ)氨基苯基尿嘧啶其中R1,R2,R3,R4和R5各自如上定义,或式(Ⅴ)化合物的酸加成物与碱金属亚硝酸盐或亚硝酸烷基酯,例如亚硝酸钠,亚硝酸钾,亚硝酸甲酯,亚硝酸正丁酯或叔丁酯,和与卤化氢(HX1),例如氯化氢或溴化氢,或者金属卤化物,例如氯化铜(Ⅰ)或氯化铜(Ⅱ)反应,并且,得到的通式(Ⅵ)重氮盐在卤化氢(HX1)存在下,例如在氯化氢或溴化氢存在下,如果适当在水存在和如果适当在最初使用的有机溶剂的存在下,在0℃和50℃之间的温度下,与通式(Ⅶ)丙烯酸衍生物反应(接原文pp.18其中R1,R2,R3,R4和R5各自如上定义,X1代表卤素,R7CH=C(R11,R12) (Ⅶ)其中R7,R11和R12各自如上定义,并且,得到的产物在稀释剂存在下,例如在N,N-二甲基甲酰胺存在下,在0℃和100℃之间的温度下,与酸受体例如氢化钠反应,得到通式(Ⅱ)链烯基苯基尿嘧啶(参见制备实施例)。
式(Ⅰa)提供了为了制备通式(Ⅰ)的化合物而在本发明方法(b)和(c)中用作起始物的羰基苯基尿嘧啶的通式定义。在式(Ⅰa)中,R1,R2,R3,R4,R5和R7各自优选地或特别地具有上文已经指出的,与说明本发明式(Ⅰ)化合物相关的,作为优选的或特别优选的R1,R2,R3,R4,R5和R7的定义。
式(Ⅰa)是本发明新的化合物;其可以通过本发明方法(a)制备。
式(Ⅲ)提供了在为了制备式(Ⅰ)化合物的本发明方法(b)中也用作起始物的氨基化合物的通式定义。在式(Ⅲ)中,R8优选地或特别地具有上文已经指出的,与说明本发明式(Ⅰ)化合物相关的,作为优选的或特别优选的R8的定义。
式(Ⅲ)起始材料是用于合成的已知化学品。
式(Ⅳa)和(Ⅳb)提供了为了制备通式(Ⅰ)的化合物而在本发明方法(c)中也用作起始物的醇或硫醇的通式定义。在式(Ⅳa)和(Ⅳb)中,Q1,Q2,R9和R10各自优选地或特别地具有上文已经指出的,与说明本发明式(Ⅰ)化合物相关的,作为优选的或特别优选的Q1,Q2,R9和R10的定义。
式(Ⅳa)和(Ⅳb)起始材料是用于合成的已知化学品。
进行本发明方法(a)至(c)的合适的稀释剂特别是惰性有机溶剂。特别包括脂肪族,脂环族或芳香族的任选卤化的烃,例如,汽油,苯,甲苯,二甲苯,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿,四氯化碳;醚类,例如***,二异丙基醚,二噁烷,四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮类,例如丙酮,丁酮,或甲基异丁基酮;腈类,例如乙腈,丙腈或丁腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基-吡咯烷酮或六甲基磷酰三胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;醇类,例如甲醇,乙醇,正-或异-丙醇,乙二醇单甲基醚,乙二醇单乙基醚,二乙二醇单甲基醚,二乙二醇单乙基醚以及它们与水的混合物或纯水。
本发明方法(a)在反应助剂存在下进行,这里优选的反应助剂是具有还原作用的化合物,例如乙酸中的锌粉,钯存在下的氢,连二亚硫酸钠和二甲硫。
进行本发明方法(a)时,反应温度可以在相当宽的范围内变化。一般情况下,方法(a)在-100℃和+50℃之间的温度下进行,优选在-80℃和+30℃之间的温度下进行。
本发明方法(a)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在本发明方法(a)的优选实施方案中,首先将式(Ⅱ)起始物加入到稀释剂中并冷却到所需温度,然后引入臭氧,直到反应终止。移去冷却浴,并计量加入反应助剂,并在需要的温度下搅拌混合物,直到反应终止。通过常规方法进行后处理(参见制备实施例)。
用于本发明方法(b)的合适的反应助剂一般是常规无机碱或有机碱或酸受体。它们优选包括碱土金属或碱金属乙酸盐,氨化物,碳酸盐,碳酸氢盐,氢化物,氢氧化物或烷氧化物,例如乙酸钠,乙酸钾或乙酸钙,氨基锂,氨基钠,氨基钾或氨基钙,碳酸钠,碳酸钾或碳酸钙,碳酸氢钾,碳酸氢钠或碳酸氢钙,氢化锂,氢化钠,氢化钾或氢化钙,氢氧化锂,氢氧化钠,氢氧化钾或氢氧化钙,甲醇钠或甲醇钾,乙醇钠或乙醇钾,正-或异丙醇钠或正-或异丙醇钾,正-、异-、仲-或叔-丁醇钠或正-、异-、仲-或叔-丁醇钾;还有碱性有机氮化合物,例如三甲胺,三乙胺,三丙胺,三丁基胺,乙基-二异丙基胺,N,N,-二甲基-环己基胺,二环己基胺,乙基-二环己基胺,N,N,-二甲基苯胺,N,N,-二甲基-苄基胺,吡啶,2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶,5-乙基-2-甲基-吡啶,4-二甲基氨基-吡啶,N-甲基哌啶,1,4-二氮杂双环[2.2.2]辛烷(DABCO),1,5-二氮杂双环[4.3.0]-壬-5-烯(DBN)或1,8-二氮杂双环[5.4.0]-十一-7-烯(DBU)。
进行本发明方法(b)时,反应温度可以在相当宽的范围内变化。一般情况下,方法(b)在0℃和150℃之间的温度下进行,优选10℃和120℃之间的温度。
本发明方法(b)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在实施本发明方法(b)时,一般以大约等摩尔量使用起始物。但是,也可以以相对大的过量使用其中之一起始物组分。反应一般在合适的稀释剂中在反应助剂存在下进行,并且反应混合物一般在需要的温度下搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
本发明方法(c)优选在反应助剂存在下进行,这里合适的反应助剂是氧化剂,例如过氧化氢,和酸例如硫酸。
进行本发明方法(c)时,反应温度可以在相当宽的范围内变化。一般情况下,方法(c)在0℃和120℃之间的温度下进行,优选在10℃和100℃之间的温度下进行。
本发明方法(c)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在本发明方法(c)的优选实施方案中,向式(Ⅰa)起始物和式(Ⅳa)或(Ⅳb)醇或硫醇的混合物中加入反应助剂,搅拌混合物,直到反应终止。通过常规方法进行后处理(参见制备实施例)。
本发明活性化合物可以用作脱叶剂,干燥剂,杀稻草剂,特别是作为杀杂草剂。从广义上说,所谓杂草被理解是在其所不期望的地点生长的所有植物。本发明物质是作为总除草剂还是选择性除草剂主要取决于使用的量。
与例如下面的植物相关,可以使用本发明活性化合物:双子叶杂草种类:芥属(sinapis),独行菜属(Lepidium),猪殃殃属(Galium),繁缕属(stellaria),母菊属(Matricaria),春黄菊属(Anthemis),辣子草(Galinsoga),藜属(Chenopodium),荨麻属(Urtica),千里光属(Senecio),苋属(Amaranthus),马齿苋属(Portulaca),苍耳属(Xanthium),旋花属(Convolvulus),甘薯属(Ipomoea),蓼属(Polygonum),田菁(sesbania),豚草属(Ambrosia),蓟属(Cirsium),飞廉属(Carduus),苦苣菜属(Sonchus),茄属(Solanum),焊菜属(Rorippa),水松叶属(Rotala),母草属(Lindernia),野芒麻属(Lamium),婆婆纳属(Veronica),苘麻属(Abutilon),刺果(Emex),曼陀罗属(Datura),堇菜属(Viola),鼬瓣花属(Galeopsis),罂粟属(Papaver),矢车菊属(Centaurea),车轴草属(Trifolium),毛茛属(Ranunculus)和蒲公英属(Taraxacum)。双子叶作物种类:棉属(Gossypium),大豆属(Glycine),甜菜属(Beta),胡萝卜属(Daucus),菜豆属(Phaseolus),豌豆属(Pisum),茄属(Solanum),亚麻属(Linum),甘薯属(Ipomoea),巢菜属(Vicia),烟草属(Nicotiana),番茄属(Lycopersicon),花生(Arachis),芥属(Brassica),莴苣属(Lactuca),香瓜属(Cucumis),和臭瓜(Cucurbita)。单子叶杂草种类:稗属(Echinochloa),狗尾草属(Setaria),黍属(Panicum),马唐属(Digitaria),梯牧属(Phleum),早熟禾属(Poa),羊茅属(Festuca),蟋蟀菜属(Eleusine),臂形草属(Brachiaria),黑麦草属(Lolium),雀麦属(Bromus),燕麦属(Avena),莎草属(Cyperus),蜀黍属(Sorghum),冰草属(Agropyron),Cycnodon,雨久花属(Monchoria),飘拂草属(Fimbristylis),慈姑(Sagittaria),荸荠属(Eleocharis),镳草(Scirpus),雀稗草(Paspalum),Ischaemum,尖瓣花属(Sphenoclea),龙爪茅属(Dactyloctenium),剪股颍属(Agrostis),看麦娘属(Alopecurus),和Apera。单子叶作物种类:稻属(Oryza),玉米属(Zea),小麦属(Triticum),大麦属(Hordeum),燕麦属(Avena),黑麦属(Secale),蜀黍属(Sorghum),黍属(Panicum),甘蔗(Saccharum),菠萝(Ananas),天门冬属(Asparagus)和葱属(Allium)。
但是,本发明活性化合物的用途绝不受这些种类的限制,而是以相同的方式扩展到其它植物。
根据浓度,本发明化合物适于例如在工业场所和铁道,有或没有树木的路或广场上全部防治杂草。这些化合物也被用来在多年生种植植物场所,草坪,运动场和牧场防治杂草,所述多年生种植植物场所例如树林,装饰性种植的树,果园,葡萄园,柠檬园,坚果园,香蕉种植园,咖啡种植园,茶种植园,橡胶种植园,油棕种植园,可可种植园,软果种植植物和蛇麻草田,以及用来在年生种植植物场所选择性防治杂草。
本发明式(Ⅰ)化合物特别适用于通过芽前和芽后方法在单子叶和双子叶农作物中选择性控制单子叶和双子叶杂草。
活性化合物可以配制成常规制剂,例如溶液、乳剂、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、和浸有活性化合物材料的天然和合成材料,以及包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与扩充剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物和氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃,如环己烷或石蜡,例如石油馏份,矿物油和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体载体是:例如铵盐,磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如,木素亚硫酸废液和甲基纤维素。
制剂中,可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如***胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
对于控制杂草,本发明活性化合物可以照原样使用或以其制剂形式,也可以作为与已知除草剂的混合物使用,可以是最终制剂或容器混合物。
适用于所述混合物的是已知的除草剂,例如N-酰苯胺类,例如吡氟草胺和敌稗;芳基羧酸类,例如二氯吡啶甲酸,麦草畏和毒莠定;芳基氧基链烷酸类,例如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草烟,2甲4氯,2甲4氯丙酸和绿草定;芳基氧基苯氧基链烷酸酯类,例如禾草灵,噁唑禾草灵,吡氟禾草灵,吡氟氯禾灵和喹禾灵;吖嗪酮类,例如杀草敏和哒草伏;氨基甲酸酯类,例如氯苯胺灵,甜菜安,甜菜宁和苯胺灵;氯代N-乙酰苯胺类,例如甲草胺,乙草安,丁草安,吡草安,异丙甲草胺,丙草安和毒草安;二硝基苯胺类,例如安磺灵,二甲戊乐灵和氟乐灵;二苯基醚类,例如三氟羧草醚,甲羧除草醚,乙羧氟草醚,氟磺胺草醚,halosafen,乳氟禾草灵和乙氧氟草醚;脲类,例如氯麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆;羟胺类,例如禾草灭,烯草酮,噻草隆,稀禾定和肟草酮;咪唑啉酮类,例如咪草烟,咪草酯,灭草烟和灭草喹;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron,苄嘧黄隆,氯嘧黄隆,氯黄隆,醚黄隆,甲黄隆,烟嘧黄隆,氟嘧黄隆,吡嘧黄隆,噻黄隆,醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,例如克草猛,灭草特,燕麦畏,茵达灭,禾草畏,草达灭,苄草丹,杀草丹和野燕畏;三嗪类,例如莠去津,氰草津,西玛津,西草净,特丁净和terbutylazine;三嗪酮类,例如环嗪酮,苯嗪草酮和嗪草酮;其它类,例如氨基***,呋草黄,灭草松,环庚草醚,异噁草酮,二氯吡啶酸,双苯唑快,氟硫草定,乙呋草黄,氟咯草酮,草铵膦,草甘膦,isoxaben,哒草特,二氯喹啉酸,喹草酸,草硫磷和灭草环。
也可能是与其它已知活性化合物的混合物,所述其它活性化合物是例如杀真菌剂,杀昆虫剂,杀螨剂,杀线虫剂,鸟驱避剂,植物营养剂和改善土壤结构的试剂。
这些活性化合物可以照原样或以其制剂形式使用,或者以通过进一步稀释而从中制备的使用形式使用,例如即用型溶液,混悬剂,乳剂,粉剂,糊剂和颗粒剂。它们可以以常规方式使用,例如通过浇灌,喷雾,弥雾或播撒。
本发明活性化合物可以在植物芽前或芽后施用。其也可以在播种前直接掺合到土壤中。
使用的活性化合物的量可以在一个基本的范围内变化。这主要取决于期望的效果的性质。一般情况下,使用的量在每公顷土壤面积使用1g-10kg活性化合物,优选每公顷土壤面积使用5g-5kg活性化合物。
下面的实施例可以说明本发明活性化合物的制备和应用。制备实施例实施例1(方法(a))向已经冷却到-70℃的8.7g(22mmol)1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和600ml二氯甲烷的混合物中通入臭氧45分钟。然后移去冷却浴,混合物与10ml二甲硫混合。一旦混合物温热至室温(大约20℃),分离各相,有机相用水洗涤,硫酸钠干燥并过滤。用水泵抽真空来浓缩滤液,残余物溶解于***,并且吸滤以分离结晶产物。
室温下(大约20℃),将1.0g(2.9mmol)1-[4-氰基-2-氟-5-甲酰基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,0.25g(3.0mmol)O-甲基-羟胺盐酸盐,0.25g(3.0mmol)乙酸钠和20ml乙醇的混合物搅拌大约90分钟。然后用水泵抽真空来浓缩混合物,并且将残余物溶解于水,与2N盐酸混合,并用***萃取。硫酸钠干燥有机相并过滤。然后用水泵抽真空小心从滤液中蒸馏出溶剂。
大约10℃下,将0.28g过氧化氢(30%浓度)和0.59g浓硫酸混合,在大约20℃下搅拌大约2小时,然后加入到1.0g(2.9mmol)1-[4-氰基-2-氟-5-甲酰基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和20ml甲醇的混合物中,反应混合物在室温下(大约20℃)搅拌大约15小时,吸滤分离结晶产物。
得到0.70g(理论量的62%)1-[4-氰基-2-氟-5-二甲氧基甲基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点164℃。
将1.8g(21mmol)丙烯酸甲酯,1.6g(15.5mmol)亚硝酸叔丁酯,1.6g(12mmol)氯化铜(Ⅱ)和50ml乙腈的混合物冷却到大约0℃,并且在该温度下向其中滴加20ml乙腈中的3.3g(10mmol)1-(5-氨基-4-氰基-2-氟-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶的溶液。然后使反应混合物温热至室温,并且在该温度下搅拌18小时。接着,加入20ml1N盐酸后,用乙酸乙酯萃取混合物,并用硫酸钠干燥有机相和过滤。浓缩滤液,并且残余物通过柱色谱处理。得到2.8g(理论量的65%)1-[4-氰基-2-氟-5-(2-氯-2-甲氧羰基-乙基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点46℃。
搅拌下向已经冷却到0℃的2.0g(4.6mmol)1-[4-氰基-2-氟-5-(2-氯-2-甲氧羰基-乙基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和30mlN,N-二甲基甲酰胺的混合物中加入0.22g氢化钠(60%浓度),反应混合物首先在0℃下搅拌15分钟,然后在20℃搅拌大约60分钟,并且最后在60℃搅拌6小时。然后水泵抽真空浓缩混合物,残余物与二异丙基醚搅拌,吸滤分离结晶产物。得到1.1g(理论量的60%)1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点154℃。式(Ⅴ)起始物实施例(V-1)
搅拌下向0.50g(1.2mmol)1-[4-氰基-2-氟-5-三氟乙酰基氨基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1ml三乙胺和50ml乙腈的混合物中加入0.17g(1.2mmol)新戊酰氯,反应混合物在20℃下搅拌18小时,再在60℃下搅拌15小时。然后水泵抽真空浓缩混合物,残余物用1N盐酸/乙酸乙酯振摇,分离有机相,硫酸钠干燥并过滤。水泵抽真空浓缩滤液,并且残余物通过柱色谱处理(硅胶,氯仿/乙酸乙酯,体积比1∶1)。
除了未反应的1-[4-氰基-2-氟-5-三氟乙酰基氨基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶(第一级分:0.30g),得到作为第二级分的0.2g(理论量的50%)1-[4-氰基-2-氟-5-氨基-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点195℃。应用实施例实施例A芽前试验溶剂: 5份重量丙酮乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
在正常土壤中播种试验植物的种子。24小时后,用活性化合物制剂对土壤喷雾。有益的是,每单位面积用的水的量保持不变。制剂中活性化合物的浓度并不重要,只有每单位面积施用的活性化合物的量是重要的。
三星期后,以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏在该项试验中,以30-125g/ha之间的比例施用时,例如制备实施例1,2和4的化合物显示出非常强的除杂草例如苋属(Amaranthus)(95%),芥属(Sinapis)(100%),苍耳属(Xanthium)(100%),马唐属(Digitaria)(80-100%),狗尾草属(Setaria)(95-100%),藜属(Chenopodium)(100%),母菊属(Matricaria)(100%),和婆婆纳属(Veronica)(100%)的除草活性,并且农作物例如玉米,大麦和棉花对它们有好的耐受性(0-30%)。实施例B芽后试验溶剂: 5份重量丙酮乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
用活性化合物制剂对高5-15cm的试验植物喷雾,使对每单位面积施用具体期望量的活性化合物。选择喷雾液的浓度,使以1000L水/公顷施用具体期望量的活性化合物。
三星期后,以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏在该项试验中,以30-125g/ha之间的比例施用时,例如制备实施例1,2和4的化合物显示出非常强的除杂草例如苘麻属(Abutilon)(100%),苋属(Amaranthus)(100%),猪殃殃属(Galium)(100%),曼陀罗属(Datura)(100%),蓼属(Polygonum)(100%)和茄属(Solanum)(100%)的活性,并且农作物例如小麦对它们中的一些有好的耐受性(10%)。
Claims (8)
1.通式(Ⅰ)取代的苯基尿嘧啶:特征在于R1代表氢,卤素或任选被取代的烷基,R2代表任选被取代的烷基,R3代表氢,氨基或者代表烷基,链烯基或炔烃基,其各自任选被取代,R4代表氢,氰基或卤素,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或任选被取代的烷基,R8代表氢,羟基,氨基或者代表烷基,烷氧基,烷基氨基,二烷基氨基,烷基羰基氨基,烷基磺酰基氨基,链烯基,链烯基氧基,炔烃基,环烷基,环烷基氧基,环烷基氨基,环烷基羰基氨基,环烷基磺酰基氨基,芳基,芳基氧基,芳基氨基,芳基羰基氨基,芳基磺酰基氨基,芳基烷基,芳基烷氧基,芳基烷基氨基,其中各基团任选被取代,并且R9和R10各自代表烷基。
2.权利要求1的通式(Ⅰ)的取代的苯基尿嘧啶,特征在于,R1代表氢,氟,氯,溴或任选被氟-和/或氯-取代的C1-C4-烷基,R2代表任选被氟-和/或氯-取代的C1-C4-烷基,R3代表氢,氨基,代表任选被氰基-,氟-,氯-或C1-C4-烷氧基-取代的C1-C6-烷基,或者代表任选被氟-和/或氯-取代的C2-C6-链烯基或C2-C6-炔烃基,R4代表氢,氰基,氟或氯,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或代表任选被卤素-或C1-C4-烷氧基-取代的C1-C4-烷基,R8代表氢,羟基,氨基,代表C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷基氨基,二-(C1-C4-烷基)-氨基,C1-C4-烷基羰基氨基或C1-C4-烷基磺酰基氨基,其中各基团任选被卤素,C1-C4-烷氧基或C1-C4-烷氧羰基取代,代表C2-C6-链烯基,C2-C6-链烯基氧基,C2-C6-炔烃基,其中各基团任选被卤素取代,代表C3-C6-环烷基,C3-C6-环烷基氧基,C3-C6-环烷基氨基,C3-C6-环烷基羰基氨基或C3-C6-环烷基磺酰基氨基,其中各基团任选被卤素或C1-C4-烷基取代,或者代表苯基,苯氧基,苯基氨基,苯基羰基氨基,苯基磺酰基氨基,苯基-C1-C4-烷基,苯基-C1-C4-烷氧基,苯基-C1-C4-烷基氨基,其中各基团任选被卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基取代,并且R9和R10各自代表C1-C4-烷基。
3.权利要求1的通式(Ⅰ)的取代的苯基尿嘧啶,特征在于,R1代表氢,氟,氯,溴或任选被氟-和/或氯-取代的甲基或乙基,R2代表任选被氟-和/或氯-取代的甲基或乙基,R3代表氢,氨基,代表各自任选被氰基-,氟-,氯-,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,正-、异-、仲或叔-丁基,或者代表任选被氟-和/或氯-取代的丙烯基,丁烯基,丙炔基或丁炔基,R4代表氢,氟或氯,R5代表氰基或硫代氨基甲酰基,和R6代表下面的基团之一:其中Q1和Q2各自代表氧或硫,R7在每种情况下代表氢或代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基或乙基,R8代表氢,羟基,氨基,代表甲基,乙基,正-或异-丙基,正-、异-、仲或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,正-、异-、仲或叔-丁氧基,甲基氨基,乙基氨基,正-或异-丙基氨基,正-、异-、仲或叔-丁基氨基,二甲基氨基,乙酰基氨基,丙酰基氨基,正-或异-丁酰基氨基,甲基磺酰基氨基或乙基磺酰基氨基,其中各基团任选被氟,氯,甲氧基,乙氧基,甲氧羰基或乙氧羰基取代,代表丙烯基,丁烯基,丙烯基氧基,丁烯基氧基,丙炔基或丁炔基,其中各基团任选被氟,氯或溴取代,代表环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基,环丙基羰基氨基,环丁基羰基氨基,环戊基羰基氨基,环己基羰基氨基,环丙基磺酰基氨基,环丁基磺酰基氨基,环戊基磺酰基氨基或环己基磺酰基氨基,其中各基团任选被氟,氯,溴,甲基或乙基取代,或者代表苯基,苯基氨基,苯基羰基氨基,苯基磺酰基氨基,苄基,苄基氧基或苄基氨基,其中各基团任选被氟,氯,溴,甲基,乙基,三氟甲基,甲氧基,乙氧基,二氟甲氧基或三氟甲氧基取代,和R9和R10各自代表甲基或乙基。
4.权利要求1的通式(Ⅰ)的取代的苯基尿嘧啶的制备方法,特征在于(a)通式(Ⅱ)的链烯基苯基尿嘧啶其中R1,R2,R3,R4,R5和R7各自如上定义,和R11和R12各自代表氢,氰基,羧基或者代表各自任选被取代的烷基或烷氧羰基,与臭氧反应,或者(b)通式(Ⅰa)的羰基苯基尿嘧啶其中R1,R2,R3,R4,R5和R7各自如上定义,与通式(Ⅲ)的氨基化合物反应,
H2N-R8 (Ⅲ)其中R8如上定义,或者与式(Ⅲ)化合物的酸加成物反应,或者(c)通式(Ⅰa)的羰基苯基尿嘧啶其中R1,R2,R3,R4,R5和R7各自如上定义,与通式(Ⅳa)或(Ⅳb)醇和/或硫醇反应,
HQ1R9 (Ⅳa) HQ2R10 (Ⅳb)其中Q1,Q2,R9和R10各自如上定义。
5.除草组合物,特征在于,其含有至少一种权利要求1的式(Ⅰ)的苯基尿嘧啶。
6.防治不期望植物的方法,特征在于,使权利要求1的通式(Ⅰ)的苯基尿嘧啶作用于不期望植物和/或其生长地域。
7.权利要求1的通式(Ⅰ)的苯基尿嘧啶控制不期望植物的用途。
8.制备除草组合物的方法,特征在于,将权利要求1的通式(Ⅰ)的苯基尿嘧啶与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19621311A DE19621311A1 (de) | 1996-05-28 | 1996-05-28 | Substituierte Phenyluracile |
DE19621311.8 | 1996-05-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1220663A true CN1220663A (zh) | 1999-06-23 |
CN1103764C CN1103764C (zh) | 2003-03-26 |
Family
ID=7795450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97195075A Expired - Fee Related CN1103764C (zh) | 1996-05-28 | 1997-05-15 | 取代的苯基尿嘧啶 |
Country Status (11)
Country | Link |
---|---|
US (2) | US6245714B1 (zh) |
EP (1) | EP0906291B1 (zh) |
JP (1) | JP2000510855A (zh) |
CN (1) | CN1103764C (zh) |
AU (1) | AU716994B2 (zh) |
BR (1) | BR9709466A (zh) |
CA (1) | CA2256415C (zh) |
DE (2) | DE19621311A1 (zh) |
ES (1) | ES2238721T3 (zh) |
IL (1) | IL126973A (zh) |
WO (1) | WO1997045418A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105682465A (zh) * | 2013-09-18 | 2016-06-15 | 瑞戴格作物保护公司 | 农业化学品 |
CN114602302A (zh) * | 2020-12-08 | 2022-06-10 | 湖北富博化工有限责任公司 | 一种硝基甲烷尾气资源化治理方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19621311A1 (de) | 1996-05-28 | 1997-12-04 | Bayer Ag | Substituierte Phenyluracile |
DE19932813A1 (de) | 1999-07-14 | 2001-01-18 | Bayer Ag | Substituierte Phenyluracile |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991000278A1 (de) | 1989-06-29 | 1991-01-10 | Ciba-Geigy Ag | Heterocyclische verbindungen |
AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5084084A (en) | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US4979982A (en) | 1990-02-02 | 1990-12-25 | Uniroyal Chemical Company, Inc. | Herbicidal cinnamic ester uracils |
JP3089621B2 (ja) | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
US5169430A (en) | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
DE4131038A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Ag | Substituierte 3-phenylurazile |
CZ287609B6 (cs) | 1991-09-23 | 2001-01-17 | Florida State University | Deriváty 10-deacetoxytaxolu |
DE4237920A1 (en) * | 1991-11-13 | 1993-05-19 | Ciba Geigy Ag | 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape |
US5336663A (en) | 1991-11-13 | 1994-08-09 | Ciba-Geigy Corporation | 3-aryluracil derivatives and their use for weed control |
US5681794A (en) | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
EP0648749B1 (de) | 1993-08-18 | 1997-12-10 | Bayer Ag | N-Cyanoaryl-Stickstoffheterocyclen |
DE4329537A1 (de) | 1993-09-02 | 1995-03-09 | Basf Ag | Substituierte 1-Amino-3-phenyluracile |
US5486521A (en) | 1994-03-21 | 1996-01-23 | Uniroyal Chemical Company, Inc. | Pyrimidinyl aryl ketone oximes |
DE19621311A1 (de) | 1996-05-28 | 1997-12-04 | Bayer Ag | Substituierte Phenyluracile |
-
1996
- 1996-05-28 DE DE19621311A patent/DE19621311A1/de not_active Withdrawn
-
1997
- 1997-05-15 DE DE59712222T patent/DE59712222D1/de not_active Expired - Fee Related
- 1997-05-15 JP JP09541495A patent/JP2000510855A/ja not_active Withdrawn
- 1997-05-15 CN CN97195075A patent/CN1103764C/zh not_active Expired - Fee Related
- 1997-05-15 ES ES97923907T patent/ES2238721T3/es not_active Expired - Lifetime
- 1997-05-15 BR BR9709466A patent/BR9709466A/pt not_active IP Right Cessation
- 1997-05-15 AU AU29555/97A patent/AU716994B2/en not_active Ceased
- 1997-05-15 EP EP97923907A patent/EP0906291B1/de not_active Expired - Lifetime
- 1997-05-15 US US09/194,629 patent/US6245714B1/en not_active Expired - Fee Related
- 1997-05-15 WO PCT/EP1997/002488 patent/WO1997045418A1/de active IP Right Grant
- 1997-05-15 IL IL12697397A patent/IL126973A/xx not_active IP Right Cessation
- 1997-05-15 CA CA002256415A patent/CA2256415C/en not_active Expired - Fee Related
-
2001
- 2001-04-24 US US09/841,361 patent/US6437126B1/en not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105682465A (zh) * | 2013-09-18 | 2016-06-15 | 瑞戴格作物保护公司 | 农业化学品 |
CN114602302A (zh) * | 2020-12-08 | 2022-06-10 | 湖北富博化工有限责任公司 | 一种硝基甲烷尾气资源化治理方法 |
CN114602302B (zh) * | 2020-12-08 | 2023-08-08 | 湖北富博化工有限责任公司 | 一种硝基甲烷尾气资源化治理方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0906291B1 (de) | 2005-03-09 |
DE59712222D1 (de) | 2005-04-14 |
ES2238721T3 (es) | 2005-09-01 |
IL126973A (en) | 2003-02-12 |
EP0906291A1 (de) | 1999-04-07 |
CN1103764C (zh) | 2003-03-26 |
DE19621311A1 (de) | 1997-12-04 |
BR9709466A (pt) | 1999-08-10 |
US6437126B1 (en) | 2002-08-20 |
CA2256415A1 (en) | 1997-12-04 |
CA2256415C (en) | 2006-10-31 |
AU716994B2 (en) | 2000-03-16 |
IL126973A0 (en) | 1999-09-22 |
WO1997045418A1 (de) | 1997-12-04 |
US6245714B1 (en) | 2001-06-12 |
JP2000510855A (ja) | 2000-08-22 |
AU2955597A (en) | 1998-01-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1234034A (zh) | 5,6-二氢-[1,4,2]-二噁嗪取代的(杂)芳基-(氧-、亚氨基-、烷基-)磺酰基氨基(硫基)羰基杂环基衍生物,它们的制法和作为除草剂的应用 | |
CN1088705C (zh) | 噻吩磺酰氨基(硫代)羰基化合物 | |
CN1239954A (zh) | 3-氨基-1-氰基苯基-尿嘧啶 | |
CN1090624C (zh) | 具有卤代烷氧基取代基的磺酰氨基羰基***啉酮类 | |
CN1145068A (zh) | 取代的磺酰氨基羰基***啉酮及其作为除草剂的应用 | |
CN1218468A (zh) | 作为除草剂的取代的芳基磺酰基氨基(硫代)羰基-***啉(硫)酮 | |
CN1293060C (zh) | 用作除草剂的取代的芳基磺酰基(硫代)脲类 | |
CN1216538A (zh) | 作为除草剂的取代的2-芳基-1,2,4-三嗪-3,5-二(硫)酮类 | |
CN1057765C (zh) | 制备4-氰基苯基亚氨基杂环化合物的中间体 | |
CN1196725A (zh) | 取代的氨基尿嘧啶 | |
CN1255126A (zh) | 具有除草作用的杂环基取代的芳香氨基化合物 | |
CN1103764C (zh) | 取代的苯基尿嘧啶 | |
CN1113063C (zh) | 杂环基尿嘧啶 | |
CN1227548A (zh) | 取代的对三氟甲基苯基尿嘧啶 | |
CN1314892A (zh) | 取代的3-芳基-吡唑类化合物 | |
CN1108250A (zh) | 取代的氨基甲酰基*** | |
CN1368971A (zh) | 取代的噻吩基(氨基)磺酰脲类化合物 | |
CN1140514C (zh) | 取代的亚氨基烷氧基苯基尿嘧啶及其制法和作为除草剂的应用 | |
CN1195339A (zh) | 4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物及其作除草剂的用途 | |
CN1101390C (zh) | 杂环基尿嘧啶 | |
CN1218469A (zh) | 用作除草剂的取代的噻吩基磺酰基(硫代)脲 | |
CN1227545A (zh) | 3-氰基芳基-吡唑及其作为除草剂的应用 | |
CN1108293C (zh) | 取代的1-氨基-3-苯基-尿嘧啶衍生物、其制备及其作为除草剂的应用 | |
CN1121394C (zh) | 取代的苯基尿嘧啶 | |
CN1227546A (zh) | 具有除草活性的取代的1-(3-吡唑基)-吡唑和用于其制备的中间体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1021368 Country of ref document: HK |
|
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |