CN1183095A - 具有卤代烷硫基取代基的磺酰氨基羧基***啉酮类 - Google Patents
具有卤代烷硫基取代基的磺酰氨基羧基***啉酮类 Download PDFInfo
- Publication number
- CN1183095A CN1183095A CN96193593A CN96193593A CN1183095A CN 1183095 A CN1183095 A CN 1183095A CN 96193593 A CN96193593 A CN 96193593A CN 96193593 A CN96193593 A CN 96193593A CN 1183095 A CN1183095 A CN 1183095A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- group
- fluorine
- chlorine
- alkoxy
- 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
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- PRZRAMLXTKZUHF-UHFFFAOYSA-N 5-oxo-n-sulfonyl-4h-triazole-1-carboxamide Chemical class O=S(=O)=NC(=O)N1N=NCC1=O PRZRAMLXTKZUHF-UHFFFAOYSA-N 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims description 135
- 229910052731 fluorine Inorganic materials 0.000 claims description 135
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 124
- 239000000460 chlorine Substances 0.000 claims description 124
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 123
- 229910052801 chlorine Inorganic materials 0.000 claims description 117
- -1 alkyl amido Chemical group 0.000 claims description 105
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 100
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 72
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 72
- 229910052794 bromium Inorganic materials 0.000 claims description 68
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 241000196324 Embryophyta Species 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 238000006467 substitution reaction Methods 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 4
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 229960004194 lidocaine Drugs 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 239000001103 potassium chloride Substances 0.000 claims description 4
- 235000011164 potassium chloride Nutrition 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 238000009333 weeding Methods 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052784 alkaline earth metal Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 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 claims 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 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 244000000004 fungal plant pathogen Species 0.000 claims 2
- 230000002508 compound effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 6
- 239000000417 fungicide Substances 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 5
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical class N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000219318 Amaranthus Species 0.000 description 4
- 244000025254 Cannabis sativa 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
- 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
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 241000405217 Viola <butterfly> Species 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 3
- 244000098897 Chenopodium botrys Species 0.000 description 3
- 235000005490 Chenopodium botrys Nutrition 0.000 description 3
- 241001478240 Coccus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241001506766 Xanthium Species 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229960005437 etoperidone Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 241000427159 Achyranthes Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000588698 Erwinia Species 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241001344131 Magnaporthe grisea Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 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
- 241000219843 Pisum Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000219295 Portulaca Species 0.000 description 2
- 241000228453 Pyrenophora 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
- 240000003829 Sorghum propinquum 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
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000221576 Uromyces Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 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
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 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
- 235000009566 rice Nutrition 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical class FCCBr JTLAIKFGRHDNQM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-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
- 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
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-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
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-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
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-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
- 241000219144 Abutilon Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 241000209136 Agropyron 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
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241001157812 Alternaria brassicicola 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
- 244000099147 Ananas comosus Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000221198 Basidiomycota Species 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
- 239000005484 Bifenox Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000611157 Brachiaria Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- 241000233684 Bremia Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 244000036828 Carduus nutans Species 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 239000005647 Chlorpropham Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 241000760356 Chytridiomycetes Species 0.000 description 1
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- LPXYXBZAXFTFKH-UHFFFAOYSA-N ClC=1C(=C(C(=NC1)C(=O)O)C(=O)O)Cl Chemical compound ClC=1C(=C(C(=NC1)C(=O)O)C(=O)O)Cl LPXYXBZAXFTFKH-UHFFFAOYSA-N 0.000 description 1
- 239000005497 Clethodim 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000186031 Corynebacteriaceae Species 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 1
- 244000024469 Cucumis prophetarum Species 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000721045 Daubentonia Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 239000005503 Desmedipham Substances 0.000 description 1
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000005507 Diflufenican Substances 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
- 241000192043 Echinochloa Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241001063191 Elops affinis Species 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- 241001517310 Eria Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 235000002756 Erythrina berteroana Nutrition 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
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241001290564 Fimbristylis Species 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- 241000816457 Galeopsis Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000219146 Gossypium 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
- 241000209219 Hordeum Species 0.000 description 1
- 241000218228 Humulus Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- 241000208822 Lactuca Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 241000228456 Leptosphaeria Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 241000209082 Lolium Species 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
- 239000005580 Metazachlor 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000005583 Metribuzin Substances 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
- 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 compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 241000233654 Oomycetes Species 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
- 235000011096 Papaver Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241001330453 Paspalum Species 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- 241001503460 Plasmodiophorida Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound 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
- 241000899394 Pseudocercospora Species 0.000 description 1
- 241000947836 Pseudomonadaceae Species 0.000 description 1
- 241000589615 Pseudomonas syringae Species 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001123569 Puccinia recondita Species 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
- 241000231139 Pyricularia Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241001633102 Rhizobiaceae Species 0.000 description 1
- 241000490453 Rorippa Species 0.000 description 1
- 241000219053 Rumex 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
- 241000221662 Sclerotinia Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000488874 Sonchus Species 0.000 description 1
- 241001674391 Sphaerulina musiva Species 0.000 description 1
- 244000273618 Sphenoclea zeylanica Species 0.000 description 1
- 235000017967 Sphenoclea zeylanica Nutrition 0.000 description 1
- 241000204060 Streptomycetaceae 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
- 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
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000722093 Tilletia caries Species 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
- 241000219793 Trifolium Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241001573053 Vandellia Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 241001251949 Xanthium sibiricum Species 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- CAWBOJFIANSPRE-UHFFFAOYSA-N [I].C(C(=O)O)(=O)O Chemical compound [I].C(C(=O)O)(=O)O CAWBOJFIANSPRE-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
- 230000000895 acaricidal effect Effects 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
- 239000000654 additive Substances 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 238000013019 agitation Methods 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- VJBCNMFKFZIXHC-UHFFFAOYSA-N azanium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical compound N.N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O VJBCNMFKFZIXHC-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003899 bactericide agent Substances 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
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 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
- 235000021028 berry Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 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
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-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
- 239000004927 clay Substances 0.000 description 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-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
- 238000004040 coloring Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000002837 defoliant Substances 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
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical class FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical class CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 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
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product 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
- 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
- 239000004459 forage Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229920005610 lignin Polymers 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
- 239000000463 material 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
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 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
- 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
- 239000001923 methylcellulose Substances 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-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
- 230000000116 mitigating effect Effects 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 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
- 239000002420 orchard Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 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
- 239000003209 petroleum derivative 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
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical class ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 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
- 230000008654 plant damage Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer 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
- 238000012805 post-processing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 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
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical class CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-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
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 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
- 150000003222 pyridines Chemical class 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
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 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
- 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 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
- 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
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及式(1)的新的磺酰氨基羰基***啉酮及式(1)化合物的盐,用于制备式(1)化合物的方法和新中间体,以及它们作为除草剂和/或杀真菌剂的应用,其中R1代表氢、羟基、氨基、亚烷基氨基或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氨基、二烷氨基、烷酰胺基、环烷基、环烷基烷基、环烷基氨基、芳基、芳烷基,R2代表被卤原子取代的烷基或链烯基,R3代表均可被任选取代的烷基、芳烷基、芳基或杂芳基。
Description
本发明涉及具有卤代烷硫基取代基新的磺酰氨基羰基***啉酮类,用于制备它们的多种方法和新中间体,以及它们作为除草剂和杀真菌剂的应用。
已知某些磺酰氨基羰基***啉酮类具有除草性能(见EP-A34148、EP-A 422469、EP-A 425948、EP-A 431291、EP-A 507171)。但是,这些化合物的活性不是在所有方面都令人满意。
R1代表氢、羟基、氨基、亚烷基氨基或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氨基、二烷氨基、烷酰氨基、环烷基、环烷基烷基、环烷基氨基、芳基、芳烷基,
R2代表卤素取代的烷基或链烯基,
R3代表均可被任选取代的以下基团:烷基、芳烷基、芳基、杂芳基。
通式(1)的具有卤代烷硫基取代基的新的磺酰氨基羰基***啉酮用以下方法得到:
R3-SO2-N=C=O (III)其中R3的定义如上,或
(b)通式(IV)的***啉酮衍生物与通式(V)的磺酰胺反应,如果合适在酸受体和稀释剂存在下进行其中R1和R2均定义如上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,
R3-SO2-NH2 (V)其中R3的定义如上,或
R3-SO2-NH-CO-Z (VI)其中R3的定义同上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,或
R3-SO2-X (VII)其中R3的定义同上,X代表卤素,
MOCN (VIII)其中M代表碱金属或碱土金属等价物,
如果需要,用常用方法将方法(a)、(b)、(c)或(d)得到的式(1)化合物转化成盐。
通式(1)的有卤代烷硫基取代基的新的磺酰氨基羰基***啉酮具有强的除草和/或杀真菌活性。
本发明优选提供式(1)化合物,其中
R1代表氢、羟基、氨基、C1-C6亚烷基氨基,或任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷羰基或C1-C4烷氧羰基取代的C1-C6烷基,或者均可被氟、氯和/或溴任选取代的C2-C6链烯基或C2-C6炔基,或者均可被氟和/或氯任选取代的C1-C6烷氨基、二(C1-C4烷基)氨基或C1-C4烷酰氨基,或者均可被氟、氯、溴和/或C1-C4烷基任选取代的C3-C6环烷基或C3-C6环烷基-C1-C4烷基,或者均可被氟、氯、溴、氰基、硝基、C1-C4烷基、三氟甲基、C1-C4烷氧基和/或C1-C4烷氧羰基任选取代的苯基或苯基C1-C4烷基,
R2代表被氟、氯和/或溴取代的C1-C6烷基或C2-C6链烯基,
R4和R5相同或不同,各自代表氢、氟、氯、溴、碘、硝基、C1-C6烷基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基、C1-C4烷基羰氧基、C1-C4烷氧羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、二(C1-C4烷基)氨基磺酰基、C3-C6环烷基或苯基取代),或C2-C6链烯基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C2-C6炔基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C1-C4烷氧基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C1-C4烷硫基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C2-C6烯氧基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),或C2-C6烯硫基(它可任选地被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基取代),C3-C6炔氧基,C3-C6炔硫基或基团-S(O)P-R6,其中
P代表数字1或2,和
R6代表C1-C4烷基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),C3-C6链烯基,C3-C6炔基,C1-C4烷氧基,C1-C4烷氧基C1-C4烷氨基,C1-C4烷氨基,二(C1-C4烷基)氨基,苯基或者基团-NHOR7,其中
R7代表C1-C12烷基(它可任选地被氟、氯、氰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基羰基、C1-C4烷氧羰基、C1-C4烷氨基羰基或二(C1-C4烷基)氨基羰基取代),或C3-C6链烯基(它可任选地被氟、氯或溴取代),C3-C6炔基,C3-C6环烷基,C3-C6环烷基C1-C2烷基,苯基C1-C2烷基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧羰基取代),或是二苯甲基或苯基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、三氟甲基、C1-C4烷氧基、C1-C2氟代烷氧基、C1-C4烷硫基、三氟甲硫基或C1-C4烷氧羰基取代),
R4和/或R5还各自代表苯基或苯氧基,或C1-C4烷基羰基氨基,C1-C4烷氧羰基氨基,C1-C4烷氨基羰基氨基,二(C1-C4烷基)氨基羰基氨基,或基团-COR8,其中
R8代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6环烷氧基、C3-C6链烯氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基C1-C4烷氨基或二(C1-C4烷基)氨基(它们均可任选地被氟和/或氯取代),
R4和/或R5还各自代表三甲基甲硅烷基、噻唑啉基、C1-C4烷磺酰氧基、二(C1-C4烷基)氨基磺酰氨基或基团-CH=N-R9,其中
R9代表任选被氟、氯、氰基、羧基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代的C1-C6烷基,或是任选被氟或氯取代的苄基,或是任选被氟或氯取代的C3-C6链烯基或C3-C6炔基,或是任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基或三氟甲硫基取代的苯基,或是任选被氟和/或氯取代的C1-C6烷氧基、C3-C6烯氧基、C3-C6炔氧基或苄氧基,或是氨基、C1-C4烷氨基、二(C1-C4烷基)氨基、苯氨基、C1-C4烷基羰基氨基、C1-C4烷氧羰基氨基、C1-C4烷基磺酰氨基,或可任选被氟、氯、溴或甲基取代的苯磺酰氨基,
或者是,
R10代表氢或C1-C4烷基,
R11和R12相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、羧基、C1-C4烷氧羰基、二甲氨基羰基、C1-C4烷磺酰基或二(C1-C4烷基)氨基磺酰基;
或者是,
或者是,
R3代表以下基团其中R15和R16相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它可任选地被氟和/或氯取代),或是氨基磺酰基、一-(C1-C4烷基)氨基磺酰基,或二-(C1-C4烷基)氨基磺酰基或C1-C4烷氧羰基或二甲氨基羰基;
或者是,
R3代表以下基团其中R17和R18相同或不同,各自代表氢、氟、氯、溴、C1-C4烷基(它可任选地被氟和/或溴取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代),或二(C1-C4烷基)氨基磺酰基;
或者是,
R3代表以下基团其中
R19和R20相同或不同,各自代表氢、氟、氯、溴、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它可任选地被氟和/或氯取代),二-(C1-C4-烷基)氨基磺酰基、C1-C4烷氧羰基或二甲氨基羰基,
A代表氧、硫或基团N-Z1,其中
Z1代表氢、C1-C4烷基(它可任选地被氟、氯、溴或氰基取代)、C3-C6环烷基、苄基、苯基(它可任选地被氟、氯、溴或硝基取代)、C1-C4烷基羰基、C1-C4烷氧羰基或二-(C1-C4烷基)氨基羰基;
或者,
R3代表以下基团
其中
R21和R22相同或不同,各自代表氢、C1-C4烷基、卤素、C1-C4烷基羰基、C1-C4烷氧基或C1-C4卤代烷氧基,
Y1代表硫或基团N-R23,其中
R23代表氢或C1-C4烷基;
或者,
R3代表以下基团其中
R24代表氢、C1-C4烷基、苄基、吡啶基、喹啉基或苯基,
R25代表氢、卤素、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、二氧戊环基或C1-C4烷氧羰基,
R26代表氢、卤素或C1-C4烷基。
另外,本发明优选提供其中的n、R1、R2、和R3均具有上述优选含义的式(1)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4烷基铵盐、二-(C1-C4-烷基)铵盐、三-(C1-C4-烷基)铵盐、四-(C1-C4-烷基)铵盐、三-(C1-C4-烷基)锍盐、C5-或C6-环烷基铵盐和二-(C1-C2-烷基)苄铵盐。
本发明特别提供了下述式(1)化合物,其中
R1代表均可任选地被氟、氯、氰基、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,或者均可被氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者甲氨基、乙氨基、正或异丙氨基、正、异、仲或叔丁氨基、二甲氨基或二乙氨基,或者均可任选地被氟、氯、溴、甲基或乙基取代的环丙基、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,或者均可任选地被氟、氯、溴、氰基、甲基、三氟甲基或甲氧基取代的苄基或苯基,
R2代表被氟和/或氯取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基、丙烯基或丁烯基,
R4代表氟、氯、溴、甲基、乙基、正或异丙基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、正或异丁氧基、二氟甲氧基、三氟甲氧基、2-氯乙氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、1,1,2,2,2-五氟乙氧基、2-甲氧-乙氧基、甲硫基、乙硫基、正或异丙硫基、正或异丁硫基、2-氟乙硫基、烯丙氧基、炔丙氧基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基、乙磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、N-甲氧基-N-甲氨基磺酰基、苯基、苯氧基、甲氧羰基、乙氧羰基、正或异丙氧羰基,
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R10代表氢,
R11代表氟、氯、溴、甲基、甲氧基、二氟甲氧基、三氟甲氧基、乙氧基、甲氧羰基、乙氧羰基、甲磺酰基或二甲氨基磺酰基,
R12代表氢,
或者,
R3代表以下基团其中R代表甲基、乙基、正或异丙基,或者
R24代表甲基、乙基、正或异丙基、苯基或吡啶基,
R25代表氢、氟、氯或溴,
R26代表氟、氯、溴、甲氧羰基或乙氧羰基。
上述的一般的或优选的基团定义适用于式(1)的最终产物,也相应地适用于各情形的制备中所需的前体或中间体。这些基团的定义可以根据需要彼此组合,从而包括了在所示优选范围之间的组合体。
在这些基团的定义中,诸如烷基、链烯基或炔基等烃基,即使是在与杂原子的组合体(如烷氧基、烷硫基或烷氨基)中,也可以是直链或支链的,虽然这一点未明确说明。
卤素一般代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
使用例如2-氯-6-甲基苯磺酰氯、4-烯丙基-5-(2,3,3-三氟丙硫基)-2,4-二氢-3H-1,2,4-***-3-酮和氰酸钠作为起始物,本发明方法(d)中的反应过程可以用以下反应式示例说明:
在本发明制备式(1)化合物的方法(a)、(c)和(d)中作为起始物使用的***啉酮的一般定义由式(II)给出。
在式(II)中,R1和R2各自优选或者特别优选具有上面关于本发明式(1)化合物的说明中作为优选或特别优选的R1和R2已经指出的那些含义。
通式(II)的***啉酮尚未在文献中公开;作为新物质,它们也构成本申请主题的一部分。
通式(II)的新的***啉酮的制备方法是,通式(IX)的巯基***啉酮和/或相应的硫氧代1,2,4-***异构体和/或相应的金属盐(特别是钠盐或钾盐)与通式(X)的烷基化试剂反应其中R1定义如上
X1-R2 (X)其中R2定义如上,X1代表卤素,优选氯、溴或碘,如果合适,反应在酸受体(如氢氧化钠)和稀释剂(如二噁烷、甲醇、乙醇、正或异丙醇和/或水)存在下于0-100℃的温度下进行(参见制备实施例)。
式(IX)中间体是已知的,和/或可以按照常规方法制备(参见EP-A 43 1291;DE-A 2250572;杂环化学杂志(J.Heterocycl.Chem.)15(1978),377-384)。
式(X)中间体也是已知的,和/或可以按照常规方法制备(参见氟化学杂志(J.Fluorine Chem.)13(1979),325;20(1982),637;21(1982),253;28(1985),291;英国化学会志Perkin会刊II(J.Chem.Soc.,Perkin II)1975,1841)。
在本发明制备式(1)化合物的方法(a)中也作为起始物使用的磺酰基异氰酸酯的一般定义由式(III)给出。
在式(III)中,R3优选或特别优选具有上面关于本发明式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义。
式(III)起始物是已知的,和/或可以用本身已知的方法制备(参见US-P 4127405,US-P 4169719,US-P 4371391,EP-A7687,EP-A 13480,EP-A21641,EP-A23141,EP-A23422,EP-A30139,EP-A 35893;EP-A 44808;EP-A 44809,EP-A 48143,EP-A 51466,EP-A64322,EP-A 70041,EP-A 173312).
在本发明制备通式(1)化合物的方法(b)中作为起始物使用的***啉酮衍生物的一般定义由式(IV)给出。在式(IV)中,R1和R2各自优选或特别优选具有上面关于式(I)化合物的说明中作为优选或特别优选的R1和R2已经指出的那些含义;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基、苯氧基、卤代或硝基苯氧基,特别是代表甲氧基、苯氧基或4-硝基苯氧基。
式(IV)起始物文献中尚未公开;作为新物质,它们也构成本申请主题的一部分。
Z-CO-Z1 (XIII)其中Z的定义同上,Z1代表卤素、烷氧基、芳基烷氧基或芳氧基,如果合适,反应在酸受体(例如氢化钠或氢化钾,氢氧化钠或氢氧化钾,叔丁醇钠或叔丁醇钾)和稀释剂(如四氢呋喃或二甲氧基乙烷)存在下或在水与有机溶剂(如二氯甲烷或氯仿)的两相体系中于0-100℃下进行。
在本发明制备通式(1)化合物的方法(b)中也作为起始物使用的磺酰胺的一般定义由式(V)给出。在式(V)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义。
式(V)起始化合物是已知的和/或可以用本身已知的方法制备(参见 US-P 4127405,US-P 4169719,US-P 4371391,EP-A 7687,EP-A 13480,EP-A 21641,EP-A 23141,EP-A 23422,EP-A 30139,EP-A 35893,EP-A 44808,EP-A 44809,EP-A 48143,EP-A 51466,EP-A64322、EP-A 70041、EP-A 173312)
在本发明制备式(1)化合物的方法(c)中作为起始物使用的磺酰胺衍生物的一般定义由式(VI)给出。在式(VI)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基或苯氧基,特别是代表甲氧基或苯氧基。
式(VI)起始物是已知的和/或可以按照本身已知的方法制备。
在本发明制备式(1)化合物的方法(d)中作为起始物使用的磺酰卤化物的一般定义由式(VII)给出。在式(VII)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义;X优选代表氟、氯或溴,特别是代表氯。
式(VII)的起始物是已知的和/或可以按照本身已知的方法制备。
用于制备式(1)新化合物的本发明方法(a)、(b)、(c)和(d)优选使用稀释剂进行。这方面合适的稀释剂实际上是所有的惰性有机溶剂。这些溶剂优选包括可任选卤化的脂族和芳族烃类,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烯、氯仿、四氯甲烷、氯苯和邻二氯苯;醚类,例如***和二丁醚、乙二醇二甲醚和二乙二醇二甲醚、四氢呋喃及二噁烷;酮类,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮;酯类,例如乙酸甲酯和乙酸乙酯;腈类,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,以及二甲基亚砜、四氢噻吩砜和六甲基磷酸三酰胺。
作为本发明方法(a)、(b)、(c)和(d)中的反应助剂和/或酸受体,可以使用通常用于此类反应的所有酸结合剂。优选碱金属氢氧化物(例如氢氧化钠和氢氧化钾),碱土金属氢氧化物(例如氢氧化钙),碱金属碳酸盐和醇盐(例如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾),以及碱性氮化合物,例如三甲胺,三乙胺,三丙胺,三丁胺,三异丁胺,二环己胺,乙基二异丙胺,乙基二环己胺,N,N-二甲基苄胺,N,N-二甲基苯胺,吡啶,2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基吡啶,1,5-二氮杂双环〔4,3,0〕-壬-5-烯(DBN),1,8-二氮杂双环〔5,4,0〕-十一碳-7-烯(DBU)和1,4-二氮杂双环〔2,2,2〕-辛烷(DABCO)。
本发明方法(a)、(b)、(c)和(d)中的反应温度可以在相当宽的范围内变化。反应一般在-20℃至+100℃的温度下进行,优选在0℃至+80℃的温度下进行。
本发明方法(a)、(b)、(c)和(d)一般在大气压下进行。但是也可以在增压或减压下进行。
为进行本发明方法(a)、(b)、(c)和(d),各种情形中所需要的起始物通常以近似等摩尔量使用。但是在每种情形也可以使用有较大过剩量的某一组分。反应一般在合适的稀释剂中于酸受体存在下进行,在所要求的特定温度下将反应混合物搅拌几小时。在本发明方法(a)、(b)、(c)和(d)中,后处理均用常用方法进行(参见制备实施例)。
如果需要,可以制备本发明通式(1)化合物的盐。这些盐可以按照简单的方式用常用的成盐方法得到,例如将式(1)化合物溶解或分散在合适的溶剂中,如二氯甲烷、丙酮、叔丁基甲基醚或甲苯中,并加入合适的碱。如果需要,在长时间搅拌后可以用浓缩或抽气过滤的方法将盐分离。
本发明化合物可以作为落叶剂、干燥剂、杀茎杆剂,尤其是作为除杂草剂使用。所谓杂草,在最广泛的含义上,应理解为生长在不应生长地方的所有植物。本发明物质是作为灭生性除草剂还是作为选择性除草剂起作用,主要取决于用量。
本发明活性化合物可用于例如以下植物:
以下各属双子叶杂草:欧白芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,蔊菜属,节节菜属,母草属,野芝麻属,婆婆纳属,苘麻属,刺酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,三叶草属,毛茛属和蒲公英属。
以下各属双子叶栽培作物:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,野豌豆属,烟草属,番茄属,花生属,芸苔属,莴苣属,黄瓜属和南瓜属。
以下各属单子叶杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,高粱属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,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。
以下各属单子叶栽培作物:稻属,玉蜀泰属,小麦属,大麦属,燕麦属,黑麦属,高粱属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
然而,本发明活性化合物的用途绝不仅限于以上各属,而是以同样的方式扩展到其它植物。
因浓度而异,这类化合物适用于诸如工业场地和铁路线上以及有或无树林的道路和广场上作灭生性除草。同样,这类化合物也可用于防治多年生栽培植物如造林带、装饰性林木、果园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶场、橡胶园、油棕园、可可园、浆果园和啤酒花田除草,草坪、草地和牧场中的杂草。另外,本发明化合物可用于一年生栽培作物中的灭生性除草和选择性除草。
本发明式(1)化合物特别适合于单子叶和双子叶栽培作物中选择性去除单子叶和双子叶杂草,可以是出苗前或出苗后。
另外,本发明活性化合物具有有效的杀微生物作用,可以实际应用于防治不良的微生物。这类活性化合物适合作为作物保护剂,特别是作为杀真菌剂使用。
植物保护中的杀真菌剂是用来防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌类的真菌。
植物保护中的杀细菌剂是用来防治假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科的细菌。
归入上述各属名称内的某些真菌性及细菌性病害的病原体可以叙述如下,但只是作为例子,而不是对它的限制:黄单孢菌属,如田野黄单孢菌稻变种;假单胞菌属,如丁香假单胞菌瓜变种;欧文氏杆菌属,如解淀欧文氏杆菌;腐霉属,如终极腐霉;疫霉属,如蔓延疫霉;假霜霉属,如葎草假霜霉或古巴假霜霉;单轴霉属,如葡萄生单轴霉;盘梗霉属,如莴苣盘梗霉;霜霉属,如豌豆霜霉或芸苔霜霉;白粉菌属,如禾白粉菌;单丝壳菌属,如苍耳单丝壳菌;柄球菌属,如苹果白粉病柄球菌;黑星菌属,如苹果黑星菌;核腔菌属,如园核腔菌或麦类核腔菌(分生孢子形式:Drechslera,同物异名:Helminthosporium);旋孢霉属,如禾旋孢霉属(分生孢子形式:Drechslera,同物异名:Helminthosporium);单胞锈菌属,如菜豆单胞锈菌;柄锈菌属,如隐匿柄锈菌;核盘菌属,如油菜核盘菌;腥黑粉菌属,如小麦网腥黑粉菌;黑粉菌属,如裸黑粉菌或燕麦黑粉菌;薄膜革菌属,如佐佐木氏薄膜革菌;梨孢属,如稻梨孢;镰孢属,如大刀镰孢;葡萄孢属,如灰色葡萄孢;壳针孢属,如颍枯壳针孢;小球腔菌属,如颍枯小球腔菌;尾孢属,如赤豆尾孢;链格孢属,如甘蓝黑斑病链格孢;小假尾孢属,如蔓毛小假尾孢。栽培作物对于为防治作物病害所需浓度的活性化合物的良好耐受性,使得有可能对植物的地上部分、无性繁殖的块茎和种子以及土壤进行处理。
式(1)化合物特别适合对苹果样的水果(如苹果)进行保护性处理,杀灭苹果白粉病的病原体(苹果白粉病柄球菌),在一定程度上还可用于杀灭稻中的稻梨孢。
这类活性化合物可以转化成常用的制剂,例如溶液、乳剂、可湿性粉剂、悬浮液、粉剂、喷粉剂、糊剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然与合成物质、以及在聚合物中的很细小的胶囊。
这些制剂用已知方法制成,例如任选地使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物与填充剂(即液体溶剂和/或固体载体)混合。
如果采用水作为填充剂,则也可以用例如有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘),氯化芳族化合物和氯化脂族烃类(如氯苯、氯乙烯或二氯甲烷),脂族烃类(如环己烷或链烷烃,例如石油馏分),矿物和植物油,醇类(如丁醇或乙二醇及它们的醚和酯),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基亚砜,以及水)。
合适的固体载体有:如铵盐和磨碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、硅镁土、蒙脱土或硅藻土)以及磨碎的合成矿物(如高度分散的二氧化硅、氧化铝和硅酸盐);适合颗粒剂的固体载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及无机或有机粗粉的合成颗粒,以及有机材料(如锯末、椰壳、玉米芯和烟草杆)的颗粒;适用的乳化剂和/或起泡剂有:如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚(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质水解产物;合适的分散剂有:木质素亚硫酸盐废液和甲基纤维素。
在制剂中可以使用增粘剂,例如羧甲基纤维素和粉末、颗粒或胶乳形式的天然及合成聚合物,如***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)和合成磷脂。其它添加剂可以是矿物和植物油。
可以使用着色剂,例如无机颜料(如氧化铁、二氧化钛和普鲁士兰)和有机染料(如茜素染料、偶氮染料和金属酞菁染料),以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1-95%重量的活性化合物,最好是0.5-90%。
为防治杂草,本发明的活性化合物本身或其制剂形式,也可以以与已知的除草剂一起的混合物、配好备用的制剂或可能的桶混物的形式使用。
可用于混合物中的组分是已知的除草剂,例如N-酰苯胺类,如吡氟草胺和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸,如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和定草酯;芳氧苯氧基链烷酸酯,如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;连氮酮类,如杀草敏和达草灭;氨基甲酸酯类,如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类,如甲草胺、乙草胺、丁草胺、吡草胺、异丙甲草胺、丙草胺和毒草胺;二硝基苯胺类,如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类,如三氟羧草醚、甲羧除草醚、乙羧除草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类,如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类,如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类,如咪草烟、咪草酯、灭草烟和灭草喹;腈类,如溴苯腈、敌草腈和碘草腈;氧乙酰胺类,如苯噻草胺;磺酰脲类,如amidosulfuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、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,如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类,如阿特拉津、草净津、西玛津、西草净、去草净和特丁津;三嗪酮类,如环嗪酮、苯嗪草酮和嗪草酮;其它,例如杀草强、呋草黄、灭草松、环庚草醚、异噁酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵磷、草甘膦、isoxaben、哒草灭、二氯喹啉酸、喹草酸、草硫磷和灭草环。
也可以与已知的其它活性化合物混合,例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱乌剂、植物营养剂和改进土壤结构的试剂。
活性化合物可以照原样、以制剂形式或者通过进一步稀释配制的使用形式(例如配好备用的溶液、悬浮液、乳液、粉末、糊和颗粒)使用。它们可以按常用方式使用,例如浇灌、喷雾、弥雾或撒施。
本发明化合物可以在植物出苗之前或之后施用。它们也可以在播种前掺加到土壤中。
活性化合物的用量可以在相当大的范围内变化。这主要取决于所要求的效果。一般来说,用量为每公顷地表面用1g-10kg活性化合物,优选每公顷5g-2kg。
将1.8g(10mmol)5-(2-氟乙硫基)-4-甲基-2,4-二氢-3H-1,2,4-***-3-酮溶在50ml乙腈中用2.65g(11mmol)2-甲氧羰基苯磺酰基异氰酸酯处理。将混合物在20℃下搅拌12小时,然后减压浓缩。残余物与异丙醇/石油醚(1∶1)一起搅拌,结晶。得到3.8g(理论值的91%)5-(2-氟乙硫基)-4-甲基-2-(2-甲氧羰基苯磺酰氨基羰基)-2,4-二氢-3H-1,2,4-***-3-酮,熔点132℃。
表1:式(1)化合物实例实施例号R1 R2 R3 熔点(℃)2 CH3 CH2-CH2-F
1703 CH3 CH2-CH2-F
1444 CH3 CH2-CH2-F
1305 CH3 CH2-CH2-F
1336 CH3 CH2-CH2-F
1517 CH3 CH2-CH2-F
1718 CH3 CH2-CH2-F
159实施例号R1 R2 R3 熔点(℃)9 CH3 CH2-CH2-F
13710 CH3 CH2-CH2-F
15811 CH3 CH2-CH2-F
14912 CH3 CH2-CH2-F
15313 CH3 CH2-CH2-F
13414 CH3 CH2-CH2-F
18115 CH3 CH2-CH2-F
121实施例号R1 R2 R3 熔点(℃)16 CH3 CH2-CH2-F
14317 CH3 CH2-CF3
13318 CH3 CH2-CF3
14719 CH3 CH2-CF3
15620 CH3 CH2-CF3
15321 CH3 CH2-CF3
15722 CH3 CH2-CF3
141实施例号R1 R2 R3 熔点(℃)23 CH3 CH2-CF3
924 CH3 CH2-CF3
11625 CH3 CH2-CF3
11226 CH3 CH2-CF3
11127 CH3 CH2-CF3
8928 CH3 CH2-CF3
14729 CH3 CH2-CF3
149实施例号R1 R2 R3 熔点(℃)30 CH3 CH2-CF3
13031 CH3 CH2-CF3
16932 CH3 CH2-CH2-CCl2-CF3 15133
CH2-F
14034
CH2-Cl
15235
CH2-CH2-F
16436
CH2-CH2-F
126实施例号R1 R2 R3 熔点(℃)37
CH2-CH2-F
14338
CH2-CH2-F
13039
CH2-CH2-F
14140
CH2-CH2-F
13441
CH2-CH2-F
15442
CH2-CH2-F
17743
CH2-CH2-F
138实施例号R1 R2 R3 熔点(℃)44
CH2-CH2-F
16145
CH2-CH2-F
12546
CH2-CH2-F
10647
CH2-CH2-F
12148
CH2-CH2-F
13349
CH2-CH2-F
15550
CH2-CH2-F
147实施例号R1 R2 R3 熔点(℃)51
CH2-CF3
14452
CH2-CF3
9553
CH2-CF3
18254
CH2-CF3
15255
CH2-CF3
11556
CH2-CF3
11757
CH2-CF
146实施例号 R1 R2 R3 熔点(℃)58
CH2-CH2-F
15159
CH2-CH2-Cl
15860 CH2-CH=CH2 CH2-CH2-F
11661 CH2-CH=CH2 CH2-CH2-F
10462 CH2-CH=CH2 CH2-CH2-F
10163 CH2-CH=CH2 CH2-CH2-F
10864 CH2-CH=CH2 CH2-CH2-F
118实施例号 R1 R2 R3 熔点(℃)65 CH3 CH2-CH2-CF3
15066 CH3 CH2-CH2-CF3
11167 CH3 CH2-CH2-CF3
14868 CH3 CH2-CHF2
14369 CH3 CH2-CHF2
12870 CH3 CH2-CHF2
13671
CH2-CH2-CF3
185实施例号 R1 R2 R3 熔点(℃)72
CH2-CH2-CF3 16673
CH2-CH2-CF3 16574
CH2-CHF2
16975
CH2-CHF2
15476
CH2-CHF2
13877 CH3 CH2-CH2-Cl
16578 CH3 CH2-CH2-Cl
146实施例号 R1 R2 R3 熔点(℃)79 CH3 CH2-CH2-Cl
14580 CH3 CH2-CH2-Cl
13981 CH3 CH2-CH2-Cl
13582 CH3 CH2-CH2-Cl
12183 CH3 CH2-CH2-Cl
17984 CH3 CH2-CH2-Cl
17885 CH3 CH2-CH2-Cl
171实施例号 R1 R2 R3 熔点(℃)86 CH3 CH2-CH2-Cl
13287 CH3 CH2-CH2-Cl
13088 CH3 CH2-CH2-Cl
14089 CH3 CH2-CH2-Cl
13990 CH3 CH2-CH2-Cl
12791 CH3 CH2-CH2-Cl
12392
CH2-CH2-Cl
174实施例号 R1 R2 R3 熔点(℃)93
CH2-CH2-Cl
13294
CH2-CH2-Cl
13595
CH2-CH2-Cl
16196
CH2-CH2-Cl
14497
CH2-CH2-Cl
15398
CH2-CH2-Cl
14099
CH2-CH2-Cl
167实施例号 R1 R2 R3 熔点(℃)100
CH2-CH2-Cl
171101
CH2-CH2-Cl
180102
CH2-CH2-Cl
152103
CH2-CH2-Cl
123104
CH2-CH2-Cl
124105
CH2-CH2-Cl
172106
CH2-CH2-Cl
132实施例号 R1 R2 R3 熔点(℃)107 CH3 CH2-CH2-Cl
147108 CH3 CH2-CH2-F
153109 CH3 CH2-CF3
147110
CH2-CF3
128111
CH2-CH2-Cl
129112
CH2-CH2-F
146113 CH3 CH2-Cl
164实施例号 R1 R2 R3 熔点(℃)114 CH3 CH2-CH2-F
138115 CH3 CH2-CH2-Cl
138116 CH3 CH2-CHF2
144117 CH3 CH2-Cl
149118 CH3 CH2-Cl
181119 CH3 CH2-Cl
180120 CH3 CH2-Cl
190实施例号R1 R2 R3 熔点(℃)121 CH3 CH2-Cl
181122
CH2-Cl
129123
CH2-Cl
157124
CH2-Cl
130125
CH2-Cl
169126
CH2-CHF2
158127 CH3 CH2-Cl
171128 CH3 CH2-CHF2
166例如,表1中作为实施例58列出的化合物可以制备如下:(用方法(b))
将1.07g(5mmol)2-烯丙氧基苯磺酰胺溶在25ml乙腈中并与0.8g(5.3mmol)二氮杂双环十一烯(DBU)搅拌混合。在20℃下30分钟后加入1.62g(5mmol)4-环丙基-5-(2-氟乙硫基)-2-苯氧羰基-2,4-二氢-3H-1,2,4-***-3-酮,将混合物再搅拌12小时。随后将反应混合物倒入冰水中,用10%浓度的盐酸酸化,用二氯乙烷萃取2次。所得残余物在用硫酸镁干燥后减压浓缩,自***中结晶。
得到1.4g(理论值的63%)2-(2-烯丙氧基苯磺酰氨基羰基)-4-环丙基-5-(2-氟乙硫基)-2,4-二氢-3H-1,2,4-***-3-酮,熔点151℃。
将4.4g(20mmol)5-(2-氯乙硫基)-4-环丙基-2,4-二氢-3H-1,2,4-***-3-酮、7.6g(24mmol)2-(N-甲氧基-N-甲氨基磺酰基)苯磺酰氯、2.6g(40mmol)氰酸钠和1.2g(15mmol)吡啶在50ml乙腈中的混合物在20℃下搅拌48小时。随后将混合物减压浓缩,油状残余物溶在二氯甲烷中用10%浓度的盐酸洗涤。有机相用硫酸镁干燥,减压浓缩,所得残余物自甲醇/异丙醇中重结晶。
得到4.7g(理论值的45%)5-(2-氯乙硫基)-4-环丙基-2-〔2-N-甲氧基-N-甲基氨基磺酰基)苯磺酰氨基羰基〕-2,4-二氢-3H-1,2,4-***-3-酮,熔点158℃。式(II)起始物实施例(II-1)
将6.6g(0.05mol)5-巯基-4-甲基-2,4-二氢-3H-1,2,4-***-3-酮溶于40ml水和40ml二噁烷中并与10g(0.25mol)氢氧化钠混合。在激烈搅拌下于80℃向该混合物通入缓和的氟里昂22(二氟氯甲烷)气流16小时。将溶液冷却,用10%浓度的盐酸调节至弱酸性pH,然后用乙酸乙酯反复萃取。将合并的有机相用硫酸镁干燥,过滤,减压浓缩。残余物自***中重结晶。
得到0.7g(理论值的7.7%)5-二氟甲硫基-4-甲基-2,4-二氢-3H-1,2,4-***-3-酮,熔点87℃。实施例(II-2)
将35.1g(0.18mol)5-巯基-4-烯丙基-2,4-二氢-3H-1,2,4-***-3-酮的钾盐溶在200ml甲醇中并与22.9g(0.18mol)1-溴-2-氟乙烷混合,在20℃下搅拌12小时。随后将混合物在60℃下再搅拌4小时,冷却,减压浓缩。残余物溶在二氯甲烷中,用10%浓度的盐酸和水洗涤。残余物减压浓缩,与石油醚一起搅拌,结晶。
抽气过滤和干燥后,得到24.8g(理论值的67.9%)4-烯丙基-5-(2-氟乙硫基)-2,4-二氢-3H-1,2,4-***-3-酮,熔点65℃。
按照实施例(II-1)和(II-2)的方法,还可以制备例如下面表2中列出的式(II)化合物。表2:式(II)化合物的实例实施例号 R1 R2 熔点(℃)II-3 CH3 CH2-CF3 132II-4 CH3 CH2-CH2-CCl2-CF3 121II-5 CH3 CH2-CH2-F 88II-6
CH2-F 116II-7
CH2-Cl 130II-8
CH2-CH2-F 120II-9
CH2-CF3 126II-10 CH3 CH2-CHF2 95II-11 CH3 CH2-CH2-CF3 144II-12
CHF2II-13
CH2-CHF2 111II-14
CH2-CH2-CF3 127II-15 CH3 CH2-FII-16 CH3 CH2-Cl 113II-17
CF3实施例号 R1 R2 熔点(℃)II-18 CH3 CF3II-19 C2H5 CF3II-20 CH2-CH=CH2 CF3II-21 CH2-CH=CH2 CH2-CHF2II-22 CH2-CH=CH2 CH2-CF3II-23
CF3II-24
CHF2II-25
CH2-FII-26
CH2-CH2-FII-27
CH2-CHF2II-28
CH2-CF3II-29 CH3 CH2-CH2-Cl 124II-30 CH2-CH=CH2 CH2-CH2-ClII-31
CH2-CH2-Cl 121II-32
CH2-CH2-ClII-33 NH2 CH2-F实施例号 R1 R2 熔点(℃)II-34 NH2 CH2-ClII-35 NH2 CH-F2II-36 NH2 CF3II-37 NH2 CH2-CH2-FII-38 NH2 CH2-CH2-ClII-39 NH2 CH2-CHF2II-40 NH2 CH2-CF3II-41 NH-CH3 CH2-FII-42 NH-CH3 CH2-ClII-43 NH-CH3 CF3II-44 NH-CH3 CH2-CH2-FII-45 NH-CH3 CH2-CH2-ClII-46 NH-CH3 CH2-CHF2II-47 NH-CH3 CH2-CF3II-48 N(CH3)2 CH2-FII-49 N(CH3)2 CH2-ClII-50 N(CH3)2 CHF2II-51 N(CH3)2 CF3II-52 N(CH3)2 CH2-CH2-FII-53 N(CH3)2 CH2-CH2-Cl实施例号 R1 R2 熔点(℃)II-54 N(CH3)2 CH2-CHF2II-55 N(CH3)2 CH2-CF3II-56 CH3 CH2-CHBr-CF3II-57 CH3 CH2-CF2-CHF-CF3 1H NMR(CDCl3.δ)
3,28(s,N-CH3),3.70
(br,t,S-CH2),4.9-
5.2(m,CHF)ppmII-58 CH3 CH2-CF2-CHF2 1H NMR(CDCl3,δ)
3.28(s,N-CH3),3.66
(t,S-CH2),5.90(tt,
将3.44g(22mmol)氯甲酸苯酯于有效的搅拌下逐滴加到3.54g(20mmol)5-(2-氟乙硫基)-4-甲基-2,4-二氢-3H-1,2,4-***-3-酮、0.9g(22mmol)氢氧化钠、0.1g(0.3mmol)溴化四丁铵、30ml水和40ml二氯甲烷的混合物中,将混合物再搅拌12小时。分离出有机相,用水洗,用硫酸镁干燥,减压浓缩,所得残余物自***中结晶。
得到5.1g(理论值的86%)5-(2-氟乙硫基)-4-甲基-2-苯氧基羰基-2,4-二氢-3H-1,2,4-***-3-酮,熔点106℃。
表3:式(IV)化合物实例实施例号 Z R1 R2 熔点(℃)IV-2
CH2-CF3 121IV-3
CH2-CH2-F 129IV-4
CH3 CH2-CF3 114IV-5
CH3 CH2-CHF2IV-6
CH3 CH2-FIV-7
CH3 CHF2IV-8
CHF2IV-9
CF3IV-10
CH2-CHF2实施例号 Z R1 R2 熔点(℃)IV-11
CH2-CH2-CF3IV-12
CH2-CF2-CHF2IV-13
CH3 CF3IV-14
CH2-CH=CH2 CH2-CH2-FIV-15
CH3 CH2-CH2-CCl2-CF3IV-16
CH2-FIV-17
CH2-ClIV-18
CH3 CH2-CH2-CF3IV-19
CH3 CH2-ClIV-20
C2H5 CF3实施例号 Z R1 R2 熔点(℃)IV-21
CH2-CH=CH2 CF3IV-22
CH2-CH=CH2 CH2-CHF2IV-23
CH2-CH=CH2 CH2-CF3IV-24
CF3IV-25
CHF2IV-26
CH2FIV-27
CH2-ClIV-28
CH2-CH2-FIV-29
CH2-CHF2IV-30
CH2-CF3实施例号 Z R1 R2 熔点(℃)IV-31
CH2-CH2-ClIV-32
CH3 CH2-CH2-ClIV-33
C2H5 CH2-CH2-ClIV-34
CH2-CH2-ClIV-35
CH2-CH=CH2 CH2-CH2-ClIV-36
NH2 CH2-FIV-37
NH2 CH2-ClIV-38
NH2 CHF2IV-39
NH2 CF3IV-40
NH2 CH2-CH2-F实施例号 Z R1 R2 熔点(℃)IV-41
NH2 CH2-CH2-ClIV-42
NH2 CH2-CHF2IV-43
NH2 CH2-CF3IV-44
NH-CH3 CH2-FIV-45
NH-CH3 CH2-ClIV-46
NH-CH3 CHF2IV-47
NH-CH3 CF3IV-48
NH-CH3 CH2-CH2-FIV-49
NH-CH3 CH2-CH2-ClIV-50
NH-CH3 CH2-CHF2实施例号 Z R1 R2 熔点(℃)IV-51
NH-CH3 CH2-CF3IV-52
N-(CH3)2 CH2-FIV-53
N-(CH3)2 CH2-ClIV-54
N-(CH3)2 CHF2IV-55
N-(CH3)2 CF3IV-56
N-(CH3)2 CH2-CH2-FIV-57
N-(CH3)2 CH2-CH2-ClIV-58
N-(CH3)2 CH2-CHF2IV-59
N-(CH3)2 CH2-CF3IV-60
CH3 CH2-CHBr-CF3实施例号 Z R1 R2 熔点(℃)IV-61
CH3 CH2-CF2-CHF-CF3IV-62
CH3 CH2-CF2-CHF2应用实施例实施例A苗前试验溶剂:5重量份丙酮乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水稀释该浓缩物至所要求的浓度。
将试验植物的种子播种在普通土壤中。24小时后,用活性化合物的制剂浇灌土壤。最好是保持每单位面积的水量恒定。制剂中活性化合物的浓度并非关键,只有每单位面积上施用的活性化合物数量才是决定性的。3周后,与未处理的对照样的生长情况相比较,将植物受损伤的程度按损伤%分级。数字表示:
%=无作用(与未处理样相近)
100%=完全摧毁
在此试验中,制备实施例5、11、17、18、21、25、33、34、35、36、37、38、39、40、43、48、49、51、52、53和54的化合物显示出强的杀灭杂草作用。
表A:苗前试验/温室
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
化合物的制备实施例编号 | 施用率(克/公顷) | 雀麦属 | 早熟禾属 | 苋属 | 牛膝菊属 | 母菊属 | 马齿苋属 | 堇菜属 |
51 | 250 | 95 | 95 | 95 | 95 | 100 | 95 | 95 |
34 | 125 | 80 | 95 | 95 | 95 | 100 | 100 | 90 |
52 | 125 | 80 | - | 90 | 95 | 90 | 60 | - |
53 | 125 | 90 | - | 90 | 95 | 90 | 80 | 80 |
54 | 125 | 90 | - | 90 | 95 | 80 | - | 60 |
33 | 125 | 95 | 95 | 95 | 95 | 95 | 95 | 90 |
17 | 125 | 95 | 95 | 95 | 95 | 95 | 100 | 95 |
18 | 125 | 95 | 90 | 80 | 90 | 60 | - | 95 |
21 | 125 | 80 | 80 | 90 | 95 | 95 | 90 | 95 |
25 | 125 | 95 | 90 | 95 | 95 | 95 | 100 | 90 |
5 | 125 | 95 | 95 | 95 | 90 | 80 | 95 | 90 |
11 | 125 | 80 | 70 | 95 | 95 | 95 | 95 | 95 |
35 | 125 | 95 | 95 | 95 | 95 | 95 | 95 | 95 |
36 | 125 | 50 | 80 | 95 | 100 | - | 95 | 90 |
37 | 125 | 95 | 60 | 95 | 100 | 95 | 100 | 95 |
38 | 125 | 80 | 60 | 95 | 100 | 100 | 90 | 95 |
39 | 125 | 95 | 95 | 95 | 95 | 95 | 100 | 95 |
40 | 125 | 60 | - | 95 | 95 | 80 | 80 | - |
43 | 125 | 80 | 70 | 95 | 100 | 95 | 95 | 95 |
48 | 125 | 95 | 95 | 95 | 95 | 95 | 95 | 70 |
49 | 125 | 90 | 95 | 95 | 95 | 95 | 80 | 90 |
为制备合适的活性化合物制剂,将1重量份活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,该浓缩物用水稀释至所要求的浓度。
高度为5-15cm的试验植物用活性化合物制剂喷雾,使得每单位面积上施加上特定数量所要的活性化合物。选择喷雾液的浓度,以便使特定数量所要的活性化合物是以每公顷2000升水的用量施用。三周后,与未处理的对照样的生长情况比较,将植物损伤程度按损伤%分级。
数字表示:
0%=无作用(与未处理的对照样相似)
100%=完全摧毁
在此试验中,制备实施例5、8、10、11、17、33、34、38、39、48、49、51、52、53和54的化合物显示出强的杀灭杂草作用。
表B:苗后试验/温室
表B:(续)
实施例c苹果白粉病保护性防治试验溶剂:4.7重量份丙酮乳化剂:0.3重量份烷基芳基聚乙二醇醚
化合物的制备实施例编号 | 施用率(克/公顷) | 苋属 | 豚草属 | 向日葵属 | 母菊属 | 茄属 | 繁缕属 | 堇菜属 | 苍耳属 |
51 | 125 | 95 | 90 | 100 | 95 | 95 | 70 | 80 | 95 |
34 | 60 | 100 | 95 | 100 | 95 | 100 | 90 | 100 | 100 |
52 | 250 | - | 80 | 100 | 90 | 70 | 95 | 60 | 80 |
53 | 250 | - | 95 | 100 | 95 | 95 | 95 | 95 | 90 |
54 | 125 | 95 | 90 | 100 | 80 | 95 | 70 | 90 | 90 |
33 | 60 | 100 | 90 | 100 | 95 | 100 | 95 | 90 | - |
17 | 60 | 90 | 90 | 80 | 50 | 80 | 70 | 50 | 90 |
5 | 125 | 95 | 90 | 80 | 95 | 95 | 90 | - | 95 |
8 | 125 | 100 | 70 | 100 | 95 | 95 | 100 | 100 | 100 |
10 | 125 | 100 | - | - | - | 95 | 90 | - | 90 |
化合物的制备实施例编号 | 施用率(克/公顷) | 苋属 | 豚草属 | 向日葵属 | 母菊属 | 茄属 | 繁缕属 | 堇菜属 | 苍耳属 |
11 | 125 | 100 | 60 | - | - | 100 | 95 | 60 | 90 |
38 | 125 | 95 | 95 | 95 | 70 | 90 | 95 | 95 | 80 |
39 | 125 | 100 | 90 | 100 | 95 | 95 | 95 | 95 | 100 |
48 | 125 | 95 | 80 | 80 | 80 | 90 | - | 90 | 70 |
49 | 125 | 100 | 90 | 100 | 90 | 80 | - | 95 | 70 |
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂及乳化剂混合,该浓缩物用水稀释至所要求的浓度。
为试验保护作用,幼小的植株用活性化合物制剂喷雾。在喷雾液层干燥后,将植株通过喷粉接种苹果白粉病病原体(苹果白粉病柄球菌)的分生孢子。
然后将植株放在温度为23℃、相对湿度约70%的温室中。
接种10天后进行评价。
在此试验中,制备实施例34和51的化合物在活性化合物浓度为100ppm时效力为98-100%。
表C
苹果白粉病保护性防治试验活性化合物 在活性化合物浓度为100ppm
Claims (10)
2、根据权利要求1的式(1)化合物及其钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4烷基铵盐、二(C1-C4烷基)铵盐、三(C1-C4烷基)铵盐、四(C1-C4烷基)铵盐、三(C1-C4烷基)锍盐、C5或C6环烷基铵盐和二(C1-C2烷基)苄铵盐,其特征在于,其中
R1代表氢、羟基、氨基、C1-C6亚烷基氨基,或任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷羰基或C1-C4烷氧羰基取代的C1-C6烷基,或者均可被氟、氯和/或溴任选取代的C2-C6链烯基或C2-C6炔基,或者均可被氟和/或氯任选取代的C1-C6烷氨基、二(C1-C4烷基)氨基或C1-C4烷酰氨基,或者均可被氟、氯、溴和/或C1-C4烷基任选取代的C3-C6环烷基或C3-C6环烷基-C1-C4烷基,或者均可被氟、氯、溴、氰基、硝基、C1-C4烷基、三氟甲基、C1-C4烷氧基和/或C1-C4烷氧羰基任选取代的苯基或苯基C1-C4烷基,
R2代表被氟、氯和/或溴取代的C1-C6烷基或C2-C6链烯基,
R3代表以下基团其中
R4和R5相同或不同,各自代表氢、氟、氯、溴、碘、硝基、C1-C6烷基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基、C1-C4烷基羰氧基、C1-C4烷氧羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、二(C1-C4烷基)氨基磺酰基、C3-C6环烷基或苯基取代),或C2-C6链烯基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C2-C6炔基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C1-C4烷氧基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C1-C4烷硫基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C2-C6烯氧基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),或C2-C6烯硫基(它可任选地被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基取代),C3-C6炔氧基,C3-C6炔硫基或基团-S(O)P-R6,其中
P代表数字1或2,和
R6代表C1-C4烷基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),C3-C6链烯基,C3-C6炔基,C1-C4烷氧基,C1-C4烷氧基C1-C4烷氨基,C1-C4烷氨基,二(C1-C4烷基)氨基,苯基或者基团-NHOR7,其中
R7代表C1-C12烷基(它可任选地被氟、氯、氰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基羰基、C1-C4烷氧羰基、C1-C4烷氨基羰基或二(C1-C4烷基)氨基羰基取代),或C3-C6链烯基(它可任选地被氟、氯或溴取代),C3-C6炔基,C3-C6环烷基,C3-C6环烷基C1-C2烷基,苯基C1-C2烷基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧羰基取代),或是二苯甲基或苯基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、三氟甲基、C1-C4烷氧基、C1-C2氟代烷氧基、C1-C4烷硫基、三氟甲硫基或C1-C4烷氧羰基取代),
R4和/或R5还各自代表苯基或苯氧基,或C1-C4烷基羰基氨基,C1-C4烷氧羰基氨基,C1-C4烷氨基羰基氨基,二(C1-C4烷基)氨基羰基氨基,或基团-COR8,其中
R8代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6环烷氧基、C3-C6链烯氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基C1-C4烷氨基或二(C1-C4烷基)氨基(它们均可任选地被氟和/或氯取代),
R4和/或R5还各自代表三甲基甲硅烷基、噻唑啉基、C1-C4烷磺酰氧基、二(C1-C4烷基)氨基磺酰氨基或基团-CH=N-R9,其中
R9代表任选被氟、氯、氰基、羧基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代的C1-C6烷基,或是任选被氟或氯取代的苄基,或是任选被氟或氯取代的C3-C6链烯基或C3-C6炔基,或是任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基或三氟甲硫基取代的苯基,或是任选被氟和/或氯取代的C1-C6烷氧基、C3-C6烯氧基、C3-C6炔氧基或苄氧基,或是氨基、C1-C4烷氨基、二(C1-C4烷基)氨基、苯氨基、C1-C4烷基羰基氨基、C1-C4烷氧羰基氨基、C1-C4烷基磺酰氨基,或可任选被氟、氯、溴或甲基取代的苯磺酰氨基,
或者是,
R10代表氢或C1-C4烷基,
R11和R12相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、羧基、C1-C4烷氧羰基、二甲氨基羰基、C1-C4烷磺酰基或二(C1-C4烷基)氨基磺酰基;
或者是,
或者是,
R3代表以下基团其中R15和R16相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它可任选地被氟和/或氯取代),或是氨基磺酰基、一(C1-C4烷基)氨基磺酰基,或二(C1-C4烷基)氨基磺酰基,C1-C4烷氧羰基或二甲氨基羰基;
或者是,
R3代表以下基团其中R17和R18相同或不同,各自代表氢、氟、氯、溴、C1-C4烷基(它可任选地被氟和/或溴取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代),或二(C1-C4烷基)氨基磺酰基;
或者是,
R19和R20相同或不同,各自代表氢、氟、氯、溴、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它可任选地被氟和/或氯取代)、二(C1-C4烷基)氨基磺酰基、C1-C4烷氧羰基或二甲氨基羰基,
A代表氧、硫或基团N-Z1,其中
Z1代表氢、C1-C4烷基(它可任选地被氟、氯、溴或氰基取代)、C3-C6环烷基、苄基、苯基(它可任选地被氟、氯、溴或硝基取代)、C1-C4烷基羰基、C1-C4烷氧羰基或二(C1-C4烷基)氨基羰基;
或者,
R3代表以下基团
其中
R21和R22相同或不同,各自代表氢、C1-C4烷基、卤素、C1-C4烷氧羰基、C1-C4烷氧基或C1-C4卤代烷氧基,
Y1代表硫或基团N-R23,其中
R23代表氢或C1-C4烷基;
或者,
R24代表氢、C1-C4烷基、苄基、吡啶基、喹啉基或苯基,
R25代表氢、卤素、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、二氧戊环基或C1-C4烷氧羰基,
R26代表氢、卤素或C1-C4烷基。
3、根据权利要求1的式(1)化合物及其盐,其特征在于,其中
R1代表均可任选地被氟、氯、氰基、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,或者均可被氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者甲氨基、乙氨基、正或异丙氨基、正、异、仲或叔丁氨基、二甲氨基或二乙氨基,或者均可任选地被氟、氯、溴、甲基或乙基取代的环丙基、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,或者均可任选地被氟、氯、溴、氰基、甲基、三氟甲基或甲氧基取代的苄基或苯基,
R2代表被氟和/或氯取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基、丙烯基或丁烯基,
R3代表以下基团其中
R4代表氟、氯、溴、甲基、乙基、正或异丙基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、正或异丁氧基、二氟甲氧基、三氟甲氧基、2-氯乙氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、1,1,2,2,2-五氟乙氧基、2-甲氧乙氧基、甲硫基、乙硫基、正或异丙硫基、正或异丁硫基、2-氟乙硫基、烯丙氧基、炔丙氧基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基、乙磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、N-甲氧基-N-甲氨基磺酰基、苯基、苯氧基、甲氧羰基、乙氧羰基、正或异丙氧羰基,
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R3代表以下基团其中
R10代表氢,
R11代表氟、氯、溴、甲基、甲氧基、二氟甲氧基、三氟甲氧基、乙氧基、甲氧羰基、乙氧羰基、甲磺酰基或二甲氨基磺酰基,
R12代表氢;
或者
R24代表甲基、乙基、正或异丙基、苯基或吡啶基,
R25代表氢、氟、氯或溴,
R26代表氟、氯、溴、甲氧羰基或乙氧羰基。
4、制备权利要求1的式(1)化合物及其盐的方法,其特征在于
R3-SO2-N=C=O (III)其中R3如权利要求1中所定义,或
R3-SO2-NH2 (V)其中R3的定义如上,或
R3-SO2-NH-CO-Z (VI)其中R3的定义同上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,或
(d)通式(II)的***啉酮与通式(VII)的磺酰卤化物及通式(VIII)的金属氰酸盐反应,如果合适,反应在反应助剂和稀释剂存在下进行其中R1和R2均定义如上,
R3-SO2-X (VII)其中R3的定义同上,X代表卤素,
MOCN (VIII)其中M代表碱金属或碱土金属等价物,
如果需要,用常用方法将方法(a)、(b)、(c)或(d)得到的式(1)化合物转化成盐。
5、除草和/或杀真菌组合物,其特征在于,其中含有至少一种权利要求1的式(1)化合物。
6、权利要求1的通式(1)化合物在防治不良植物和/或植物病原真菌方面的应用。
7、防治杂草和/或植物病原真菌的方法,其特征在于,使权利要求1的通式(1)化合物作用于杂草或真菌或其栖息地上。
8、制备除草和/或杀真菌组合物的方法,其特征在于,将权利要求1的通式(1)化合物与填充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19508119.6 | 1995-03-08 | ||
DE19508119A DE19508119A1 (de) | 1995-03-08 | 1995-03-08 | Sulfonylaminocarbonyltriazolinone mit Halogenalkylthio-Substituenten |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1183095A true CN1183095A (zh) | 1998-05-27 |
CN1090183C CN1090183C (zh) | 2002-09-04 |
Family
ID=7755969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96193593A Expired - Fee Related CN1090183C (zh) | 1995-03-08 | 1996-03-01 | 具有卤代烷硫基取代基的磺酰氨基羧基***啉酮类 |
Country Status (12)
Country | Link |
---|---|
US (2) | US5994273A (zh) |
EP (1) | EP0869948B1 (zh) |
JP (1) | JPH11501308A (zh) |
KR (1) | KR19980702807A (zh) |
CN (1) | CN1090183C (zh) |
AU (1) | AU4831496A (zh) |
BR (1) | BR9607235A (zh) |
CA (1) | CA2214792A1 (zh) |
DE (2) | DE19508119A1 (zh) |
ES (1) | ES2160801T3 (zh) |
HU (1) | HUP9800820A3 (zh) |
WO (1) | WO1996027591A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102336743A (zh) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | 取代***啉酮醚类化合物及其应用 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19525162A1 (de) | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
USRE39607E1 (en) | 1995-07-11 | 2007-05-01 | Bayer Aktiengesellschaft | Herbicidal sulphonylamino(thio) carbonyl compounds |
DE19802697A1 (de) | 1998-01-24 | 1999-07-29 | Bayer Ag | Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen |
DE10031825A1 (de) | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
DE10117673A1 (de) * | 2001-04-09 | 2002-10-10 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylamino(thio)carbonyl-triazolin(thi)one |
DE10143083A1 (de) * | 2001-09-03 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
DE10201391A1 (de) | 2002-01-16 | 2003-07-31 | Bayer Cropscience Ag | Verwendung von Alkoholethoxylaten als Penetrationsförderer |
DE102008016813B4 (de) | 2008-04-01 | 2021-08-12 | Tesa Scribos Gmbh | Holographischer Datenspeicher |
EP2371823A1 (de) | 2010-04-01 | 2011-10-05 | Bayer CropScience AG | Cyclopropyl-substituierte Phenylsulfonylamino(thio)carbonyltriazolinone, ihre Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
WO2014202510A1 (de) | 2013-06-20 | 2014-12-24 | Bayer Cropscience Ag | Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH573203A5 (zh) * | 1973-03-19 | 1976-03-15 | Ciba Geigy Ag | |
US4098896A (en) * | 1975-09-29 | 1978-07-04 | Chevron Research Company | 1-Halohydrocarbylthio-3-hydrocarbylthio-4-substituted-1,2,4-delta2 -triazolidin-5-ones |
DE3815765A1 (de) * | 1988-05-09 | 1989-11-23 | Bayer Ag | 2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel |
DE3936623A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber schwefel gebundenen substituenten |
US5085684A (en) * | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
US5057144A (en) * | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
DE3836623A1 (de) * | 1988-10-27 | 1990-05-03 | Chemex Gmbh | Brechkern fuer speiser |
US5238910A (en) * | 1989-11-03 | 1993-08-24 | Bayer Aktiengesellschaft | Herbicidal halogenated sulphonylaminocarbonyltriazolinones |
-
1995
- 1995-03-08 DE DE19508119A patent/DE19508119A1/de not_active Withdrawn
-
1996
- 1996-03-01 ES ES96904086T patent/ES2160801T3/es not_active Expired - Lifetime
- 1996-03-01 JP JP8526587A patent/JPH11501308A/ja not_active Ceased
- 1996-03-01 US US08/894,932 patent/US5994273A/en not_active Expired - Fee Related
- 1996-03-01 BR BR9607235A patent/BR9607235A/pt not_active Application Discontinuation
- 1996-03-01 HU HU9800820A patent/HUP9800820A3/hu unknown
- 1996-03-01 KR KR1019970706214A patent/KR19980702807A/ko active IP Right Grant
- 1996-03-01 EP EP96904086A patent/EP0869948B1/de not_active Expired - Lifetime
- 1996-03-01 AU AU48314/96A patent/AU4831496A/en not_active Abandoned
- 1996-03-01 WO PCT/EP1996/000834 patent/WO1996027591A1/de active IP Right Grant
- 1996-03-01 DE DE59607101T patent/DE59607101D1/de not_active Expired - Fee Related
- 1996-03-01 CN CN96193593A patent/CN1090183C/zh not_active Expired - Fee Related
- 1996-03-01 CA CA002214792A patent/CA2214792A1/en not_active Abandoned
-
1999
- 1999-08-04 US US09/368,379 patent/US6153761A/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102336743A (zh) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | 取代***啉酮醚类化合物及其应用 |
CN102336743B (zh) * | 2010-07-20 | 2015-01-14 | 中国中化股份有限公司 | 取代***啉酮醚类化合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
WO1996027591A1 (de) | 1996-09-12 |
EP0869948A1 (de) | 1998-10-14 |
CA2214792A1 (en) | 1996-09-12 |
HUP9800820A2 (hu) | 1998-07-28 |
JPH11501308A (ja) | 1999-02-02 |
US5994273A (en) | 1999-11-30 |
KR19980702807A (ko) | 1998-08-05 |
BR9607235A (pt) | 1997-11-11 |
ES2160801T3 (es) | 2001-11-16 |
HUP9800820A3 (en) | 2000-03-28 |
CN1090183C (zh) | 2002-09-04 |
AU4831496A (en) | 1996-09-23 |
DE19508119A1 (de) | 1996-09-12 |
EP0869948B1 (de) | 2001-06-13 |
DE59607101D1 (de) | 2001-07-19 |
US6153761A (en) | 2000-11-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1038129C (zh) | 取代的***啉酮类化合物、其制备方法及其应用 | |
CN1105712C (zh) | N-氰芳基氮杂环化合物 | |
CN1148852A (zh) | 取代的二氮杂环己烷二(硫)酮 | |
CN1090623C (zh) | 具有除草性质的3-芳基-1,2,4-***衍生物 | |
CN1090183C (zh) | 具有卤代烷硫基取代基的磺酰氨基羧基***啉酮类 | |
CN1183094A (zh) | 具有卤代烷氧基取代基的磺酰氨基羰基***啉酮类 | |
CN1088063C (zh) | 磺酰氨基(硫代)羰基-1,2,4-***啉(硫)酮衍生物及制备方法和作为除草剂的应用 | |
JPH05279351A (ja) | イソオキサゾールカルボン酸誘導体 | |
CN1168668A (zh) | 通过氧和硫结合取代基的磺酰氨基羰基***啉酮 | |
CN1079398C (zh) | 作为除草剂的取代的芳基磺酰基氨基(硫代)羰基-***啉(硫)酮 | |
CN1075061C (zh) | 杂环基苄腈 | |
JPH05213907A (ja) | スルホニルアミノカルボニルトリアゾリノン及びその製造方法 | |
CN1057765C (zh) | 制备4-氰基苯基亚氨基杂环化合物的中间体 | |
KR100291842B1 (ko) | 플루오로벤족사졸릴옥시아세트아미드 | |
CN1070855C (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 | |
JPH06184119A (ja) | 複素環式トリアゾリノン | |
JP3237802B2 (ja) | フルオロベンゾチアゾリルオキシアセトアミド類 | |
KR100353848B1 (ko) | 신규한2-(7-클로로-2-벤족사졸릴옥시)-아세트아미드 | |
EP0537539A1 (de) | 2-(2-Benzoxazolyl-oxy)-acetamide und ihre Verwendung als Herbicides | |
JPH09512281A (ja) | アルキルスルフィニル及びアルキルスルホニル−1,2,4−チアジアゾリルオキシアセトアミド及びその除草剤としての使用 | |
CN1220663A (zh) | 取代的苯基尿嘧啶 | |
EP0537543A1 (de) | 2-(2-(Fluorphenyl)-1,3,4-thiadiazol-5-yl-oxy)-acetamide verwendbar als Herbizide | |
JPH05213892A (ja) | ジアリールピラゾリノン及びその製造法 | |
US5288694A (en) | N-aryl-nitrogen heterocycles | |
AU700589B2 (en) | Herbicidal sulphonylamino(thio)carbonyltriazolin(thi)ones having heterocyclyl(alk)oxy substituents |
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 | ||
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 |