CN1239954A - 3-氨基-1-氰基苯基-尿嘧啶 - Google Patents
3-氨基-1-氰基苯基-尿嘧啶 Download PDFInfo
- Publication number
- CN1239954A CN1239954A CN97180458A CN97180458A CN1239954A CN 1239954 A CN1239954 A CN 1239954A CN 97180458 A CN97180458 A CN 97180458A CN 97180458 A CN97180458 A CN 97180458A CN 1239954 A CN1239954 A CN 1239954A
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- China
- Prior art keywords
- group
- alkyl
- halogen
- amino
- uridylic
- Prior art date
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- Granted
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- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000003118 aryl 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 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- -1 carboxyl- Chemical group 0.000 claims description 87
- 241000196324 Embryophyta Species 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- VJBXRBCLVIKDFG-UHFFFAOYSA-N 5-amino-1-hydroxycyclohexa-2,4-diene-1-carbonitrile Chemical compound NC1=CC=CC(O)(C#N)C1 VJBXRBCLVIKDFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 244000025254 Cannabis sativa Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 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 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-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
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 240000008853 Datura stramonium Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 235000004429 Matricaria chamomilla var recutita Nutrition 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005594 Phenmedipham Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 235000000208 Solanum incanum Nutrition 0.000 description 2
- 241000209072 Sorghum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
- 239000006185 dispersion Substances 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 2
- 230000002650 habitual effect Effects 0.000 description 2
- UTJJFHJHTZKQSW-UHFFFAOYSA-N humulane Chemical compound CC1CCCC(C)CCC(C)(C)CCC1 UTJJFHJHTZKQSW-UHFFFAOYSA-N 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- 229940088649 isoxaflutole Drugs 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 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
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 150000002696 manganese Chemical class 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
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- QTGVGIVRLSGTJJ-UHFFFAOYSA-N n-(acetamidomethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CNC(C)=O)C(=O)CCl QTGVGIVRLSGTJJ-UHFFFAOYSA-N 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 compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 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
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 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
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000008188 pellet Substances 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 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
- 238000005554 pickling Methods 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 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
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 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
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-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
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber 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
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- 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
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 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
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
-
- 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
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
新的式(I)的3-氨基-1-氰基苯基-尿嘧啶,其中R1表示氢或表示在各种情况下可选择取代的烷基、链烯基、链炔基、环烷基、环烷基烷基、芳基、芳烷基、杂环基或杂环基烷基,R2表示氢,氰基或卤素,R3表示氢,卤素或可选择取代的烷基,R4表示可选择取代的烷基,制备这类化合物的方法和它们作为除草剂的用途。
Description
本发明涉及新的3-氨基-1-氰基苯基-尿嘧啶,其制备工艺以及作为除草剂的用途。
已经知道某些3-烷基-1-氰基苯基-尿嘧啶具有除草的特性(参见EP-A0 473 551)。例如,2-氰基-5-[3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶基]-4-氟-苯甲酸异丙酯可用于防治杂草。然而,在低用量时,这种物质的效力不总是令人满意的。
因此,本发明提供新的3-氨基-1-氰基苯基-尿嘧啶,
其中
R1表示氢或在各种情况下可选择取代的烷基,链烯基,链炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R2表示氢,氰基或卤素,
R3表示氢,卤素或可选择取代的烷基,
R4表示可选择取代的烷基。
其中R1,R2,R3和R4均如上述定义,
如果合适的话,在酸结合剂存在时以及如果合适的话,在稀释剂存在时,与一亲电的氨化剂反应。
最后,还发现新的式(I)3-氨基-1-氰基苯基-尿嘧啶具有很好的除草特性。
令人惊讶的是本发明式(I)的3-氨基-1-氰基苯基-尿嘧啶与2-氰基-5-[3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶基]-4-氟-苯甲酸异丙酯相比,有好得多的除草活性,该化合物是现有技术中的一种具有类似结构和同样的作用目的的活性化合物。
在定义中,饱和或不饱和的烃链,如烷基,烯基或炔基,在所有情况下都是直链或支链。
卤素通常表示氟,氯,溴或碘,优选氟,氯或溴,特别优选氟或氯。
式(I)提供了本发明的3-氨基-1-氰基苯基-尿嘧啶的一般定义。优选的是下面的式(I)的化合物,其中
R1表示氢或可选择地被氰基-,羧基-,氢-,C1-C4-烷氧基-或C1-C4-烷氧基-羰基-取代的含有1-6个碳原子的烷基或
表示在各种情况下可选择地被氰基-,羧基-或C1-C4-烷氧基-羰基-取代的并在所有情况下含有2-6个碳原子的链烯基或链炔基,或
表示在各种情况下在环烷基基团含有3-6个碳原子以及可选择地在烷基部分含有1-4个碳原子的环烷基或环烷基烷基,它们在各种情况下可选择地被相同或不同的取代基单取代至四取代,该取代基选自氰基、羧基、卤素、C1-C4-烷基和C1-C4-烷氧基-羰基,或
表示在芳基基团含有6或10个碳原子和可选择地在烷基部分含有1-4个碳原子的芳基或芳烷基,它们在各种情况下可选择地被相同或不同取代基单取代至三取代,该取代基选自硝基、氰基、羧基、卤素、C1-C4-烷基、卤素-C1-C4-烷基、C1-C4-烷氧基、卤素-C1-C4-烷氧基和/或C1-C4-烷氧基-羰基,或
表示选自下组的杂环基或杂环基烷基,包括环氧丙烷基(Oxexanyl)、呋喃基、呋喃甲基、四氢呋喃基、四氢呋喃甲基、噻吩基、噁唑基、异噁唑基、噻唑基、吡唑基、噁二唑基,吡啶基、吡啶甲基,其中每个基团都是可选择地被相同或不同的取代基单取代至三取代,该取代基选自氰基、羧基、卤素、C1-C4-烷基、卤素-C1-C4-烷基、C1-C4-烷氧基和/或卤素-C1-C4-烷氧基,
R2表示氢,氰基,氟,氯或溴,
R3表示氢,氟,氯,溴或表示含有1-4个碳原子,可选择地被相同或不同的取代基单取代至五取代的烷基,上述取代基选自氟、氯和溴,和
R4表示含有1-4个碳原子的烷基或表示含有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基。
特别优选的是下面的式(I)化合物,其中
R1表示氢或表示可选择地被氰基,羧基,氟,氯,甲氧基,乙氧基,丙氧基,甲氧基羰基,乙氧基羰基或丙氧基羰基取代的甲基,乙基,正或异丙基,正、异、仲或叔丁基,或
表示在各种情况下可选择地被氰基,羧基,甲氧基羰基或乙氧基羰基取代的丙烯基,丁烯基,丙炔基或丁炔基,或
表示环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,它们各自都可以可选择地被相同或不同的取代基单取代至四取代,取代基选自氰基,羧基,氟,氯,甲基,乙基,甲氧基羰基和乙氧基羰基,或
表示苯基或苄基,它们都可以可选择地被相同或不同的取代基单取代至三取代,取代基选自硝基,氰基,羧基,氟,氯,甲基,乙基,三氟甲基,甲氧基,乙氧基,二氟甲氧基,三氟甲氧基,甲氧基羰基和乙氧基羰基,或
表示杂环基或杂环基烷基,其选自下组的环氧丙烷基、呋喃基、呋喃甲基、四氢呋喃基、四氢呋喃甲基、噻吩基、噁唑基、异噁唑基、噻唑基、吡唑基、噁二唑基,吡啶基、吡啶甲基,其中每个基团都是可选择地被相同或不同的取代基单取代至三取代,该取代基选自氰基、羧基、氟,氯,甲基,乙基,三氟甲基,甲氧基,乙氧基,二氟甲氧基和三氟甲氧基,
R2表示氢,氟或氯,
R3表示氢,氟,氯,甲基,乙基或表示含有1或2个碳原子和1-3个氟和/或氯原子的卤代烷基
R4表示甲基,乙基或表示含有1或2个碳原子和1-5个氟和/或氯原子的卤代烷基。
上述的一般或优选的基团定义不仅适用于式(I)的终产物,还相对地适用于在各种情况下制备工艺所需的起始物或中间体。这些基团的定义可以彼此结合,即包括给定的优选范围之间的结合。
本发明的式(I)化合物的实施例列于下组。
其中R1具有下列含义:
氢,甲基,乙基,正或异丙基,正、异、仲或叔丁基,正、异、仲或叔戊基,氟乙基,氯乙基,氯氟乙基,二氟乙基,二氯乙基,三氟乙基,三氯乙基,氯二氟乙基,氟丙基,氯丙基,二氟丙基,二氯丙基,三氟丙基,三氯丙基,氰基乙基,氰基丙基,氰基丁基,羧甲基,羧乙基,羧丙基,羧丁基,甲氧基甲基,乙氧基甲基,丙氧基甲基,甲氧基乙基,乙氧基乙基,丙氧基乙基,甲氧基丙基,乙氧基丙基,丙氧基丙基,甲氧基羰基甲基,乙氧基羰基甲基,丙氧基羰基甲基,甲氧基羰基乙基,乙氧基羰基乙基,丙氧基羰基乙基,甲氧基羰基丙基,乙氧基羰基丙基,丙氧基羰基丙基,1-丙烯-3-基(烯丙基),3-甲基-1-丙烯-3-基,2-丁烯-4-基(丁烯基),1-丙炔-3-基(炔丙基),3-甲基-1-丙炔-3-基,2-丁炔-4-基,环丙基,氰基环丙基,羧基环丙基,二氟环丙基,二氯环丙基,甲基环丙基,甲氧基羰基环丙基,乙氧基羰基环丙基,环丁基,氰基环丁基,羧基环丁基,二氟环丁基,三氟环丁基,四氟环丁基,氯三氟环丁基,甲基环丁基,环戊基,氰基环戊基,羧基环戊基,氟代环戊基,氯代环戊基,二氟环戊基,二氯环戊基,甲基环戊基,甲氧基羰基环戊基,乙氧基羰基环戊基,环己基,氰基环己基,羧基环己基,氟代环己基,氯代环己基,二氟环己基,二氯环己基,甲基环己基,三氟甲基环己基,甲氧基羰基环己基,乙氧基羰基环己基,环丙基甲基,二氟环丙基甲基,二氯环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,氰基环己基甲基,羧基环己基甲基,氟代环己基甲基,氯代环己基甲基,甲基环己基甲基,三氟甲基环己基甲基,苯基,氰基苯基,羧基苯基,硝基苯基,氟代苯基,氯代苯基,溴代苯基,甲基苯基,三氟甲基苯基,甲氧基苯基,二氟甲氧基苯基,三氟甲氧基苯基,甲氧基羰基苯基,乙氧基羰基苯基,苄基,氰基苄基,羧基苄基,氟代苄基,氯代苄基,甲基苄基,三氟甲基苄基,甲氧基苄基,二氟甲氧基苄基,三氟甲氧基苄基,甲氧基羰基苄基,乙氧基羰基苄基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,环氧丙烷基,噁唑基,异噁唑基。
第2组
其中R1的含义如第一组中所述。
第3组
其中R1的含义如第一组中所述。
第4组
其中R1的含义如第1组中所述。
其中R1的含义如第1组中所述。
其中R1的含义如第1组中所述。
其中R1的含义如第1组中所述。
其中R1的含义如第1组中所述。
其中R1的含义如第1组中所述。
使用1-(4-氰基-3-甲氧基羰基-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶作为起始物,1-氨基氧代-2,4-二硝基-苯作为亲电的氨化剂,本发明工艺中的反应过程可以通过下列反应式说明:
式(II)提供了1-氰基苯基-尿嘧啶的一般定义,该化合物在本发明方法中作为起始物。在上式中,R1,R2,R3和R4各自优选或特别优选的含义是那些在关于本发明式(I)的化合物的叙述中已经提到的优选的或特别优选的基团。
式(II)的1-氰基苯基-尿嘧啶是已知的或原则上可根据已知的工艺来制备(参见EP-A 0473551)。
进行本发明方法所需的合适的亲电氨化剂都是惯用的适合于引入一个氨基基团的物质。实例包括1-氨基氧代-2,4-二硝基-苯(=2,4-二硝基-苯基-羟胺)和羟胺-O-磺酸。
实施本发明方法所需的合适的酸结合剂都是惯用的无机和有机碱。优选使用碱金属或碱土金属的乙酸盐,氨化物,碳酸盐,碳酸氢盐,氢化物,氢氧化物或醇盐,例如乙酸钠,乙酸钾或乙酸钙,氨基化锂,氨基化钠,氨基化钾或氨基化钙,碳酸钠,碳酸钾或碳酸钙,碳酸氢钠,碳酸氢钾或碳酸氢钙,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,甲醇化钠或甲醇化钾,乙醇化钠或乙醇化钾,正或异丙醇化钠或钾,正、异、仲或叔丁醇化钠或钾;而且还包括碱性的有机氮化合物,例如三甲基胺,三乙基胺,三丙基胺,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-2-二甲基-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)和1,8-二氮杂双环-[5,4,0]-十一碳-7-烯(DBU)。
实施本发明工艺所需的合适的稀释剂都是惯用的惰性有机溶剂。优选使用脂族、脂环族和芳香族的可选择卤化的烃类,例如戊烷,己烷,庚烷,石油醚,石油英,轻汽油,苯,甲苯,二甲苯,氯苯,二氯苯,环己烷,甲基环己烷,二氯甲烷,三氯甲烷(氯仿)或四氯化碳,此外还有二烷基醚,例如乙醚,二异丙基醚,甲基叔丁基醚,乙基叔丁基醚,甲基叔戊基醚(MTBE),乙基叔戊基醚,四氢呋喃(THF),1,4-二噁烷,乙二醇二甲醚或乙二醇二乙醚,二乙二醇二甲醚或二乙二醇二乙醚;此外还有二烷基酮,如丙酮,甲丁酮(甲基乙基酮),甲基异丙基酮或甲基异丁基酮,还有腈类,如乙腈,丙腈,丁腈或苯甲腈;还有酰胺类,如N,N-二甲基甲酰胺(DMF),N,N-二甲基-乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;还有酯类,如乙酸甲酯,乙酸乙酯,乙酸正或异丙酯,乙酸正、异或仲丁酯;还有亚砜,如二甲基亚砜;还有醇类,如甲醇,乙醇,正或异丙醇,正-、异-、仲或叔丁醇,乙二醇一甲基醚或乙二醇一乙基醚,二乙二醇一甲基醚或二乙二醇一乙基醚;以及它们与水或纯水的混合物。
当实施本发明工艺方法时,反应温度可以在相对较宽的范围内变动。通常,反应温度在-20℃至+100℃之间,优选0℃至80℃,特别优选20℃至60℃。
本发明的工艺通常在大气压下进行。然而,也可以在有所升高或降低的压力下进行-通常在0.1bar-10bar之间。
为实施本发明方法,使用的起始物通常是大致上等摩尔量的。然而,其中的一种化合物的使用也可以相对过量。反应通常在合适的稀释剂中有酸结合剂的存在下进行,反应化合物通常在要求的温度下搅拌几个小时。根据惯用的方法进行后处理(参见制备实施例)。
本发明的活性化合物可用于脱叶剂,干燥剂,除草剂,特别是除杂草剂。广义的杂草可以理解为生长在不被希望的地方的所有植物。本发明的物质是否起到灭杀性或选择性除草剂的作用基本上取决于用量。
本发明的活性化合物可以用于例如下列植物:
双子叶杂草属:芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,辣子草属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,甘薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,蔊菜属,水松叶属,母草属,野芝麻属,婆婆纳属,苘麻属,刺果属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,车轴草属,毛茛属和蒲公英属。
双子叶作物属:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,甘薯属,巢菜属,烟草属,番茄属,花生属,油菜属,莴苣属,刺瓜属和臭瓜属。
单子叶杂草属:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊矛属,牛筋草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,蜀黍属,冰草属,狗牙根属,鸭舌草属,飘拂草属,慈姑属,针蔺属,蔗草属,雀稗属,鸭嘴草属,尖瓣花属,龙爪茅属,剪股颍属,看麦娘属和风草属。
单子叶作物属:稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,蜀黍属,黍属,甘蔗属,菠萝属,芦笋属和葱属。
然而,本发明的活性化合物的使用决不限于这些属的植物,还可以同样地扩大到其它植物。
取决于使用浓度,这些化合物适合于全面防治例如在工业地带,铁轨,有或无树木的道路和广场的杂草。同样,这些化合物可用于防治多年生栽培地的杂草,例如森林,观赏性树木的栽培地,果园,葡萄园,柑橘林,坚果园,香蕉种植园,咖啡种植园,茶叶种植园,橡胶种植园,油棕种植园,可可种植园,小果栽培地和啤酒花地,草地,马场和牧场,以及选择性防治一年生和多年生栽培地的杂草。
本发明式(I)的化合物特别适合于在出苗前和出苗后,选择性防治单子叶和多子叶杂草。
活性化合物可以制成惯用的制剂,如溶液剂,乳剂,可温性粉剂,悬浮剂,粉剂,粉尘剂,糊剂,可溶性粉剂,颗粒剂,浓悬浮乳剂,浸渍了活性化合物的天然和合成材料,以及在聚合物中的微细胶囊。
这些剂型是按照已知的方式制得的,例如混合活性化合物与填充剂,填充剂是一种液体溶剂和/或固体载体,以及可选择地使用表面活性剂,表面活性剂是一种乳化剂和/或分散剂和/或泡沫形成剂。
如果使用的填充剂是水,还可以使用例如有机溶剂作为助剂。基本上,适用的液体溶剂是:芳香烃类,如二甲苯、甲苯或烷基萘,氯化芳香烃和氯化脂族烃类,如氯苯、氯乙烯或二氯甲烷,脂族烃类,如环己烷或石蜡,例如石油馏分、矿物油和植物油,醇类,如丁醇或乙二醇以及它们的醚和酯类,酮类,如丙酮、甲基乙基酮、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基亚砜,还有水。
适用的固体载体是:例如铵盐和磨碎的天然矿物,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,磨碎的合成矿物,如细分散二氧化硅、氧化锂和硅酸盐;用于颗粒剂的合适的固体载体是:例如碾碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及无机合成颗粒和有机粉,有机材料颗粒,如锯屑、椰壳粉、玉米芯和烟草杆;合适的乳化剂和/或泡沫剂是: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,烷基磺酸酯,烷基硫酸酯,芳基磺酸酯和蛋白水解产物;合适的分散剂是:例如木质素-亚硫酸废液和甲基纤维素。
可用于制剂中的粘合剂如羧甲基纤维素和天然及合成的以粉末、颗粒或乳胶形式存在的聚合物,如阿拉伯树胶,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,和合成的磷脂。其它可能的添加剂是矿物油和植物油。
可以使用着色剂,如无机颜料,例如氧化铁,二氧化钛和普鲁士蓝,以及有机染料,如茜素染料,偶氮染料和金属酞菁染料,以及微量营养素,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂通常含有0.1%-95%重量百分比的活性化合物,优选0.5%-90%。
为防治杂草,本发明的活性化合物可以其本身或以制剂的形式使用,还可以与已知的除草剂混合物、最终的制剂或桶混形式使用。
在一些情况下,可能出现增效作用。
混合物中其它可能的成分可以是已知的除草剂,例如:乙草胺,氟锁草醚(钠盐),苯草醚,草不绿,枯杀达(钠盐),莠灭净,amidochlor,amidosulfuron,黄草灵,阿特拉津,azimsulfuron,草除灵,呋草黄,苄嘧黄隆(甲基),噻草平,吡草酮,新燕灵(乙基),双丙氨酰膦,治草醚,溴丁酰草胺,杀草全,溴苯腈,丁草胺,丁草特,cafenstrole,长杀草,甲氟除草醚,草灭平,杀草敏,氯嘧黄隆(乙基),草枯醚,绿黄隆,绿麦隆,恶庚草烷,醚黄隆,烯草酮,clodinafop(-propargyl),广灭灵,二氯吡啶酸,clopyrasulfuron,cloransulam(-methyl),cumyluron,草津净,草灭特,cyclosulfamuron,噻草酮,cyhalofop(丁基),2,4-滴,2,4-滴丁酸,2,4-滴丙酸,异苯敌草,燕麦敌,麦草畏,氯甲草(甲基),苯敌快,吡氟草胺,dimefuron,哌草丹,克草胺,戊草净,dimethenamid,敌乐胺,草乃敌,敌草快阳离子,氟硫草定,敌草隆,香草隆,茵达灭,禾草畏,丁氟消草,ethametsulfuron(甲基),灭草呋喃,ethoxyfen,etobenzanid,唑禾草灵,氟燕灵(异丙基),强氟燕灵(L-异丙基),甲氟燕灵(甲基),啶嘧黄隆,吡氟禾草灵(丁基),flumetsulam,flumiclorac(pentyl),flumioxazin,flumipropyn,伏草隆,氟咯草酮,乙羧氟草醚,胺草唑,flupropacil,抑草丁,氟草同,氟草定,调嘧醇,呋草酮,氟磺胺草醚,草铵膦(铵盐),草甘膦(异丙基铵盐),克阔乐,吡氟乙草灵(乙氧基乙基),六嗪同,咪草酯(甲基),imazamethapyr,imazamox,灭草烟,灭草喹,普杀特,imazosulfuron,碘苯腈,异乐灵,异丙隆,异恶草胺,isoxaflutole,恶草醚,克阔乐,环草定,利谷隆,2甲4氯,2甲4氯丙酸,苯噻草胺,苯嗪草,吡草胺,噻唑隆,metobenzuron,秀谷隆,丙草安,metosulam,甲氧隆,赛克津,甲黄隆(甲基),草达灭,绿谷隆,萘丙胺,草萘胺,草不隆,烟嘧黄隆,达草灭,坪草丹,黄草消,恶草灭,氟硝草醚,百草枯,胺硝草,苯敌草,哌草膦,丙草胺,氟嘧黄隆(甲基),扑草净,毒草安,敌稗,喔草酯,拿草特,苄草丹,prosulfuron,吡唑特,吡嘧黄隆(乙基),苄草唑,稗草畏,哒草特,pyrithiobac(钠盐),快杀稗,喹草酸,喹禾灵(乙基),喹禾灵(-p-tefuryl),rimsulfuron,稀禾定,西玛津,西草净,sulcotrione,sulfentrazone,嘧黄隆,sulfosate,牧草胺,丁唑隆,特丁津,去草净,thenylchlor,thiafluamide,thiazopyr,thidiazimin,噻黄隆,灭草丹,丁草威,肟草酮,野草畏,醚苯黄隆,苯黄隆(甲基),绿草定,灭草环,氟乐灵和triflusulfuron。
也可以与其它已知的活性化合物,如杀菌剂,杀虫剂,杀螨剂,杀线虫剂,鸟类驱避剂,植物营养素和能改善土壤结构调节剂混合使用。
活性化合物可以以其自身单独使用,以它们的制剂形式或由此进一步稀释制备的使用形式使用,如现用溶液,悬浮剂,乳剂,粉剂,糊剂和颗粒剂。它们按照惯用的方式使用,例如灌水,喷洒,喷雾或撒布。
本发明的活性化合物在植物的苗前或苗后均可施用。它们还可以在播种前混入土壤中使用。
活性化合物的用量可以在相当大的范围内变化。这主要取决于期望达到的效果的性质。通常,用量在1g-10Kg活性化合物/公顷土壤表面,优选在5g-5Kg/公顷。
本发明活性化合物的制备和使用可以从下面的实施例中了解。
制备实施例:
含有1.3g(3.38mmol)的1-(4-氰基-2-氟代-5-异丙氧基羰基-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶,0.76g(3.38mmol)的1-氨基氧代-2,4-二硝基-苯,0.33g碳酸氢钠和10ml N,N-二甲基甲酰胺的混合物在室温下(接近20℃)搅拌12天,每隔一天加入1.2g 1-氨基氧代-2,4-二硝基-苯和1.0g碳酸氢钠。然后将混合物倒入0.1%浓度的氢氧化钠水溶液中,用乙醚提取。有机相先用0.1%浓度的氢氧化钠溶液冲洗,然后用1N盐酸洗,用硫酸钠干燥和过滤。滤液在水泵真空下浓缩,残留物用3ml乙醚消化,得到的结晶产品用吸滤分离。
这样就得到了0.45g(理论值的33%)的3-氨基-1-(4-氰基-2-氟代-5-异丙氧基羰基-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶,熔点166℃。
3.0g(13.5mmol)的5-氨基-2-氰基-4-氟代-苯甲酸异丙酯溶于50ml丙酮,然后滴加与3.2g(16mmol)的氯甲酸三氯甲酯(双光气)混合。混合物在室温下搅拌1小时,随后在水泵真空下浓缩。残留物溶于甲苯,然后在-30℃逐滴加到含有3.3g(13.5mmol)的3-氨基-4,4,4-三氟代-丁烯酸乙酯,0.52g氢化钠,20ml甲苯和30mlN,N-二甲基甲酰胺的混合物中。反应混合物在-30℃搅拌20分钟,然后倒入水中,加入乙醚振摇,用1N盐酸酸化,再加入乙酸乙酯振荡。有机相用水洗,用硫酸钠干燥和过滤。滤液在水泵真空下浓缩,残留物用乙醚消化,得到的结晶产品用吸滤分离。
这样就得到了1.6g(理论值的32%)的1-(4-氰基-2-氟代-5-异丙氧基羰基-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶,熔点120℃。
使用上述方法,还可以制备列于表1中的式(I)化合物。
表1(续)
使用实施例:
实施例A:
苗前试验:
溶剂:5重量份的丙酮
乳化剂:1重量份的烷基芳基聚乙二醇醚
为制备出合适的活性化合物的制剂,将1重量份的活性化合物与上述重量的溶剂混合,加入上述重量的乳化剂,浓缩物以水稀释至希望的浓度。
试验植物的种子播种于普通土壤中。大约24小时后,将活性化合物的制剂喷洒到土壤中,使每单位面积施用特定混合量的所需活性化合物。选择喷雾液的浓度以使得在每公顷的1000L水中使用所需特定量的活性化合物。
三周后,植物的损伤度与未处理的对照的发育相比较,以损伤的百分比评定。
数字表示:
0%=无影响(同未处理的对照)
100%=完全损坏
在这一试验中,制备实施例1中的化合物在30g/ha的用量下,显示出对一些杂草有超过90%的活性。
表A:苗前试验/温室制备实施例中的化合物 用量 稗 蜀黍 苘麻 曼陀罗 母菊
(g ai./ha)(1) 30 100 95 100 100 100
实施例B:
苗后试验:
溶剂:5重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备出合适的活性化合物的制剂,将1重量份的活性化合物与上述重量的溶剂混合,加入上述重量的乳化剂,浓缩物以水稀释至希望的浓度。
试验植物高度为5-15cm,将活性化合物的制剂喷洒其上,使每单位面积施用特定混合量的所需活性化合物。选择喷雾液的浓度以使得在每公顷1000L水中使用所需特定量的活性化合物。
三周后,植物的损伤度与未处理的对照的发育相比较,以损伤的百分比评定。
数字表示:
0%=无影响(同未处理的对照)
100%=完全破坏
在这一试验中,制备实施例1中的化合物在30g/ha的用量下,显示出对一些杂草有100%的效果。
表B:苗后试验/温室制备实施例中的化合物 用量 看麦娘 雀麦 狗尾草 苘麻 曼陀罗 母菊
(1) 30 100 100 100 100 100 100
Claims (7)
1.式(I)的3-氨基-1-氰基苯基-尿嘧啶
其中
R1表示氢或在各种情况下可选择取代的烷基,链烯基,链炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R2表示氢,氰基或卤素,
R3表示氢,卤素或可选择取代的烷基,
R4表示可选择取代的烷基。
2.根据如权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶,其中
R1表示氢或可选择地被氰基-,羧基-,卤素-,C1-C4-烷氧基-或C1-C4-烷氧基-羰基-取代的含有1-6个碳原子的烷基或
表示在各种情况下可选择地被氰基-,羧基-或C1-C4-烷氧基-羰基-取代的并且在各种情况下含有2-6个碳原子的链烯基或链炔基,或
表示在各种情况下在环烷基基团含有3-6个碳原子以及可选择地在烷基部分含有1-4个碳原子的环烷基或环烷基烷基,它们在各种情况下可选择地被相同或不同的取代基单取代至四取代,该取代基选自氰基、羧基、卤素、C1-C4-烷基和C1-C4-烷氧基-羰基,或
表示在芳基基团含有6或10个碳原子和可选择地在烷基部分含有1-4个碳原子的芳基或芳烷基它们且在各种以及在所有情况下可选择地被相同或不同取代基单取代至三取代,该取代基选自硝基、氰基、羧基、卤素、C1-C4-烷基、卤素-C1-C4-烷基、C1-C4-烷氧基、卤素-C1-C4-烷氧基和/或C1-C4-烷氧基-羰基,或
表示选自下组的杂环基或杂环基烷基,包括环氧丙烷基、呋喃基、呋喃甲基、四氢呋喃基、四氢呋喃甲基、噻吩基、噁唑基、异噁唑基、噻唑基、吡唑基、噁二唑基,吡啶基、吡啶甲基,其中每个基团都是可选择地被相同或不同的取代基单取代至三取代,该取代基选自氰基、羧基、卤素、C1-C4-烷基、卤素-C1-C4-烷基、C1-C4-烷氧基和/或卤素-C1-C4-烷氧基,
R2表示氢,氰基,氟,氯或溴,
R3表示氢,氟,氯,溴或表示含有1-4个碳原子,可选择地被相同或不同的取代基单取代至五取代的烷基,该取代基选自氟、氯和溴,和
R4表示含有1-4个碳原子的烷基或表示含有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基。
3.根据权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶的制备方法,其特征在于将式(II)的1-氰基苯基-尿嘧啶
其中R1,R2,R3和R4均如上述定义,
如果适合的话,在酸结合剂存在时以及如果适合的话,在稀释剂存在时,与一亲电的氨化剂反应得到3-氨基-1-氰基苯基-尿嘧啶。
4.除草组合物,其特征在于包含至少一种如权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶。
5.使用根据权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶防治杂草。
6.防治杂草的方法,其特征在于将根据权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶施用于杂草和/或其生活环境。
7.制备除草组合物的方法,其特征在于将根据权利要求1所述的式(I)的3-氨基-1-氰基苯基-尿嘧啶与填充剂和/或表面活性剂混合。
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US20220274954A1 (en) | 2019-07-22 | 2022-09-01 | Bayer Aktiengesellschaft | Substituted n-phenyl-n-aminouarcils and salts thereof and use thereof as herbicidal agents |
BR112021026526A2 (pt) | 2019-07-22 | 2022-04-26 | Bayer Ag | N-feniluracilas substituídas, sais das mesmas e seu uso como agentes herbicidas |
AU2021334085A1 (en) | 2020-08-24 | 2023-03-23 | Bayer Aktiengesellschaft | Substituted N-phenyluracils and salts thereof, and use thereof as herbicidal active substances |
EP4230620A1 (de) | 2022-02-22 | 2023-08-23 | Bayer Aktiengesellschaft | Substituierte n-amino-n´-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2023161172A1 (de) | 2022-02-22 | 2023-08-31 | Bayer Aktiengesellschaft | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
EP4230621A1 (de) | 2022-02-22 | 2023-08-23 | Bayer AG | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104952A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cyclopropyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104954A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104956A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkylsulfanylphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795549A (fr) * | 1972-02-18 | 1973-08-16 | Bayer Ag | Nouveaux 1-aminouraciles et leurs sels, leur procede de preparation et leur application comme herbicides |
EP0473551A1 (de) * | 1990-08-31 | 1992-03-04 | Ciba-Geigy Ag | 3-Aryluracil-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Unkrautbekämpfungsmittel |
US5266554A (en) | 1990-08-31 | 1993-11-30 | Ciba-Geigy Corporation | Heterocyclic compounds |
AU2448292A (en) * | 1992-08-21 | 1994-03-15 | Nissan Chemical Industries Ltd. | Pyrimidine derivative and weedkiller |
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 |
DE4440914A1 (de) * | 1994-11-17 | 1996-05-23 | Bayer Ag | Substituierte Diazacyclohexandi(thi)one |
DE19604229A1 (de) | 1995-02-09 | 1996-08-14 | Ciba Geigy Ag | Neue Herbizide |
-
1996
- 1996-12-09 DE DE19651036A patent/DE19651036A1/de not_active Withdrawn
-
1997
- 1997-11-27 BR BR9714388-0A patent/BR9714388A/pt not_active Application Discontinuation
- 1997-11-27 CA CA002274119A patent/CA2274119A1/en not_active Abandoned
- 1997-11-27 US US09/319,280 patent/US6175010B1/en not_active Expired - Fee Related
- 1997-11-27 JP JP52615098A patent/JP2001506613A/ja not_active Withdrawn
- 1997-11-27 EP EP97951989A patent/EP0942905B1/de not_active Expired - Lifetime
- 1997-11-27 CN CN97180458A patent/CN1107057C/zh not_active Expired - Fee Related
- 1997-11-27 DK DK97951989T patent/DK0942905T3/da active
- 1997-11-27 DE DE59706453T patent/DE59706453D1/de not_active Expired - Fee Related
- 1997-11-27 ES ES97951989T patent/ES2172029T3/es not_active Expired - Lifetime
- 1997-11-27 WO PCT/EP1997/006618 patent/WO1998025909A1/de active IP Right Grant
- 1997-11-27 AU AU55569/98A patent/AU722601B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
CA2274119A1 (en) | 1998-06-18 |
EP0942905A1 (de) | 1999-09-22 |
JP2001506613A (ja) | 2001-05-22 |
DK0942905T3 (da) | 2002-06-10 |
AU722601B2 (en) | 2000-08-10 |
DE19651036A1 (de) | 1998-06-10 |
EP0942905B1 (de) | 2002-02-20 |
CN1107057C (zh) | 2003-04-30 |
ES2172029T3 (es) | 2002-09-16 |
WO1998025909A1 (de) | 1998-06-18 |
US6175010B1 (en) | 2001-01-16 |
BR9714388A (pt) | 2000-05-16 |
DE59706453D1 (de) | 2002-03-28 |
AU5556998A (en) | 1998-07-03 |
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