ZA200101563B - Benzoyl derivatives, method for producing them and their use as herbicides and plant growth regulators. - Google Patents
Benzoyl derivatives, method for producing them and their use as herbicides and plant growth regulators. Download PDFInfo
- Publication number
- ZA200101563B ZA200101563B ZA200101563A ZA200101563A ZA200101563B ZA 200101563 B ZA200101563 B ZA 200101563B ZA 200101563 A ZA200101563 A ZA 200101563A ZA 200101563 A ZA200101563 A ZA 200101563A ZA 200101563 B ZA200101563 B ZA 200101563B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- unsubstituted
- alkylamino
- substituted
- group
- Prior art date
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title claims description 24
- 239000004009 herbicide Substances 0.000 title description 5
- 239000005648 plant growth regulator Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 nitro-substituted phenyl Chemical group 0.000 claims description 169
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 6
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 244000045561 useful plants Species 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 3
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000004986 diarylamino group Chemical group 0.000 claims description 3
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000005367 heteroarylalkylthio group Chemical group 0.000 claims description 3
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 3
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 239000011630 iodine Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 2
- 125000006801 haloalkenylamino group Chemical group 0.000 claims 2
- 125000006812 haloalkenylaminocarbonyl group Chemical group 0.000 claims 2
- 125000006776 haloalkenylcarbonyl group Chemical group 0.000 claims 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 2
- 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims 2
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims 2
- 125000006804 haloalkynylamino group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 claims 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000006788 haloalkenyloxycarbonyl group Chemical group 0.000 claims 1
- 125000006814 haloalkynylaminocarbonyl group Chemical group 0.000 claims 1
- 125000006779 haloalkynylcarbonyl group Chemical group 0.000 claims 1
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims 1
- 125000006785 haloalkynyloxycarbonyl group Chemical group 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 230000009261 transgenic effect Effects 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 3
- XBYZOHTXPQOOJM-UHFFFAOYSA-N 1,2-oxazol-3-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=CON=1 XBYZOHTXPQOOJM-UHFFFAOYSA-N 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000000676 alkoxyimino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- RDEMLCQKHALULB-UHFFFAOYSA-N 2-formyl-3-oxo-3-phenylpropanenitrile Chemical compound O=CC(C#N)C(=O)C1=CC=CC=C1 RDEMLCQKHALULB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004580 4,5-dihydroimidazol-2-yl group Chemical group N1C(=NCC1)* 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000016680 Dioxygenases Human genes 0.000 description 1
- 108010028143 Dioxygenases Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19840337A DE19840337A1 (de) | 1998-09-04 | 1998-09-04 | Benzoylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200101563B true ZA200101563B (en) | 2002-05-10 |
Family
ID=7879793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200101563A ZA200101563B (en) | 1998-09-04 | 2001-02-26 | Benzoyl derivatives, method for producing them and their use as herbicides and plant growth regulators. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6297196B1 (pt) |
| EP (1) | EP1109807A1 (pt) |
| JP (1) | JP2002524459A (pt) |
| KR (1) | KR20010085762A (pt) |
| CN (1) | CN1149211C (pt) |
| AR (1) | AR020376A1 (pt) |
| AU (1) | AU752786B2 (pt) |
| BR (1) | BR9913461A (pt) |
| CA (1) | CA2343151A1 (pt) |
| CO (1) | CO5210935A1 (pt) |
| CZ (1) | CZ2001796A3 (pt) |
| DE (1) | DE19840337A1 (pt) |
| HU (1) | HUP0104201A3 (pt) |
| ID (1) | ID29626A (pt) |
| IL (1) | IL141374A0 (pt) |
| MY (1) | MY130252A (pt) |
| PL (1) | PL346496A1 (pt) |
| RU (1) | RU2223271C2 (pt) |
| SK (1) | SK2962001A3 (pt) |
| TR (1) | TR200100695T2 (pt) |
| TW (1) | TW585863B (pt) |
| UA (1) | UA68395C2 (pt) |
| WO (1) | WO2000014087A1 (pt) |
| ZA (1) | ZA200101563B (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010040838A (ko) | 1998-12-11 | 2001-05-15 | 고지마 아끼로, 오가와 다이스께 | 이미드 화합물 촉매를 이용한 유기 화합물의 제조법 |
| DE19950943A1 (de) | 1999-10-22 | 2001-05-17 | Aventis Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Hemmstoffe der Hydroxyphenylpyruvat-Dioxygenase |
| WO2007079346A2 (en) * | 2005-12-30 | 2007-07-12 | Olsen Christopher J | Articulated wheel assemblies and vehicles therewith |
| WO2008014430A1 (en) | 2006-07-27 | 2008-01-31 | Emisphere Technologies, Inc. | Arylsulfanyl compounds and compositions for delivering active agents |
| JP5511693B2 (ja) * | 2009-02-03 | 2014-06-04 | クミアイ化学工業株式会社 | 縮合環化した２−ピリドン誘導体及び除草剤 |
| MX2013010395A (es) | 2011-03-15 | 2013-10-01 | Bayer Ip Gmbh | Amidas de acido n-(1,2,5-oxadiazol-3-il)-, n-tetrazol-5-il)- y n-(triazol-5-il)bicicloaril-carboxilico y su uso como herbicidas. |
| CN103992301B (zh) * | 2014-05-09 | 2016-01-13 | 上海大学 | 2-羟基-5-氧代-4-芳基-2-三氟甲基-3,4,5，6，7,8-六氢-2h-色烯-3-羧酸乙酯化合物的制备方法 |
| US10745396B2 (en) | 2015-07-01 | 2020-08-18 | Syngenta Participations Ag | Pesticidally active polycyclic derivatives with sulfur containing substituents |
| BR112018001518B1 (pt) * | 2015-07-24 | 2021-03-23 | Bayer Cropscience Aktiengesellschaft | Derivados de furano-/tienocicloalquilamino-2-pirimidina substituído e uso dos mesmos para o controle de crescimento indesejado de plantas |
| CN107398300B (zh) * | 2017-07-24 | 2020-08-21 | 中国科学院化学研究所 | 芳香族酰胺芳环c-h键直接氨基化反应的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2134257T3 (es) | 1992-03-03 | 1999-10-01 | Idemitsu Kosan Co | Derivado de pirazol. |
| CA2117413C (en) * | 1993-07-30 | 2006-11-21 | Neil Geach | Herbicidal isoxazole-4-yl-methanone derivatives |
| WO1995013275A1 (fr) * | 1993-11-09 | 1995-05-18 | Idemitsu Kosan Co., Ltd. | Derives de pyrazole et herbicide les contenant |
| GB9405229D0 (en) * | 1994-03-17 | 1994-04-27 | Rhone Poulenc Agriculture | Compositions of matter |
| AU2753695A (en) * | 1994-06-27 | 1996-01-19 | Idemitsu Kosan Co. Ltd | Herbicidal composition |
| WO1996025413A1 (en) * | 1995-02-15 | 1996-08-22 | Idemitsu Kosan Co., Ltd. | Isoxazole derivatives |
| CA2215057A1 (en) | 1995-04-05 | 1996-10-10 | Hiroshi Yamamoto | Pyrazole derivatives |
| AU6777896A (en) * | 1995-08-25 | 1997-03-19 | E.I. Du Pont De Nemours And Company | Bicyclic herbicides |
| WO1997012885A1 (fr) * | 1995-10-04 | 1997-04-10 | Idemitsu Kosan Co., Ltd. | Derives de pyrazole |
| AU7227296A (en) * | 1995-10-09 | 1997-04-30 | Idemitsu Kosan Co. Ltd | 2-cyano-1,3-dione derivatives and herbicides containing the same as active ingredient |
| WO1997023135A1 (fr) * | 1995-12-25 | 1997-07-03 | Idemitsu Kosan Co., Ltd. | Composition herbicide |
| US6297198B1 (en) * | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| WO1997044340A1 (fr) * | 1996-05-23 | 1997-11-27 | Idemitsu Kosan Co., Ltd. | Derives d'isoxazole |
-
1998
- 1998-09-04 DE DE19840337A patent/DE19840337A1/de not_active Withdrawn
-
1999
- 1999-08-26 PL PL99346496A patent/PL346496A1/xx not_active IP Right Cessation
- 1999-08-26 JP JP2000568845A patent/JP2002524459A/ja active Pending
- 1999-08-26 AU AU58551/99A patent/AU752786B2/en not_active Ceased
- 1999-08-26 BR BR9913461-6A patent/BR9913461A/pt not_active IP Right Cessation
- 1999-08-26 HU HU0104201A patent/HUP0104201A3/hu unknown
- 1999-08-26 ID IDW20010469A patent/ID29626A/id unknown
- 1999-08-26 TR TR2001/00695T patent/TR200100695T2/xx unknown
- 1999-08-26 EP EP99946028A patent/EP1109807A1/de not_active Withdrawn
- 1999-08-26 UA UA2001042216A patent/UA68395C2/uk unknown
- 1999-08-26 RU RU2001109229/04A patent/RU2223271C2/ru not_active IP Right Cessation
- 1999-08-26 CA CA002343151A patent/CA2343151A1/en not_active Abandoned
- 1999-08-26 SK SK296-2001A patent/SK2962001A3/sk unknown
- 1999-08-26 WO PCT/EP1999/006259 patent/WO2000014087A1/de not_active Application Discontinuation
- 1999-08-26 IL IL14137499A patent/IL141374A0/xx unknown
- 1999-08-26 KR KR1020017002867A patent/KR20010085762A/ko not_active Application Discontinuation
- 1999-08-26 CN CNB998105945A patent/CN1149211C/zh not_active Expired - Fee Related
- 1999-08-26 CZ CZ2001796A patent/CZ2001796A3/cs unknown
- 1999-08-27 CO CO99054357A patent/CO5210935A1/es not_active Application Discontinuation
- 1999-09-02 TW TW088115146A patent/TW585863B/zh not_active IP Right Cessation
- 1999-09-02 AR ARP990104413A patent/AR020376A1/es not_active Application Discontinuation
- 1999-09-02 US US09/388,905 patent/US6297196B1/en not_active Expired - Fee Related
- 1999-09-03 MY MYPI99003819A patent/MY130252A/en unknown
-
2001
- 2001-02-26 ZA ZA200101563A patent/ZA200101563B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL346496A1 (en) | 2002-02-11 |
| EP1109807A1 (de) | 2001-06-27 |
| AR020376A1 (es) | 2002-05-08 |
| MY130252A (en) | 2007-06-29 |
| AU752786B2 (en) | 2002-10-03 |
| UA68395C2 (en) | 2004-08-16 |
| HUP0104201A2 (hu) | 2002-03-28 |
| CA2343151A1 (en) | 2000-03-16 |
| TR200100695T2 (tr) | 2001-07-23 |
| TW585863B (en) | 2004-05-01 |
| RU2223271C2 (ru) | 2004-02-10 |
| HUP0104201A3 (en) | 2002-04-29 |
| WO2000014087A1 (de) | 2000-03-16 |
| US6297196B1 (en) | 2001-10-02 |
| ID29626A (id) | 2001-09-06 |
| CZ2001796A3 (cs) | 2001-08-15 |
| JP2002524459A (ja) | 2002-08-06 |
| SK2962001A3 (en) | 2001-11-06 |
| DE19840337A1 (de) | 2000-03-09 |
| IL141374A0 (en) | 2002-03-10 |
| CO5210935A1 (es) | 2002-10-30 |
| CN1149211C (zh) | 2004-05-12 |
| BR9913461A (pt) | 2001-07-24 |
| CN1317004A (zh) | 2001-10-10 |
| KR20010085762A (ko) | 2001-09-07 |
| AU5855199A (en) | 2000-03-27 |
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