KR20240051198A - 농약제로서 신규 피라지닐-트리아졸 화합물 - Google Patents

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Publication number

KR20240051198A

KR20240051198A KR1020247009430A KR20247009430A KR20240051198A KR 20240051198 A KR20240051198 A KR 20240051198A KR 1020247009430 A KR1020247009430 A KR 1020247009430A KR 20247009430 A KR20247009430 A KR 20247009430A KR 20240051198 A KR20240051198 A KR 20240051198A

Authority

KR

South Korea

Prior art keywords

spp

methyl

ethyl

cyclopropyl

pyrazine

Prior art date

2021-08-25

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.)

Pending

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• LQTPJFKKSLWSNB-UHFFFAOYSA-N 2-(2h-triazol-4-yl)pyrazine Chemical class C1=NNN=C1C1=CN=CC=N1 LQTPJFKKSLWSNB-UHFFFAOYSA-N 0.000 title abstract description 3
• 239000000575 pesticide Substances 0.000 title description 29
• 239000000203 mixture Substances 0.000 claims abstract description 121
• 241000238631 Hexapoda Species 0.000 claims abstract description 60
• 241001465754 Metazoa Species 0.000 claims abstract description 59
• 241000607479 Yersinia pestis Species 0.000 claims abstract description 57
• 238000009472 formulation Methods 0.000 claims abstract description 41
• -1 1-cyanocyclopropyl Chemical group 0.000 claims description 388
• 150000001875 compounds Chemical class 0.000 claims description 250
• 238000000034 method Methods 0.000 claims description 68
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 239000000460 chlorine Substances 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 30
• 150000002431 hydrogen Chemical class 0.000 claims description 30
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
• NIPZZXUFJPQHNH-UHFFFAOYSA-M pyrazine-2-carboxylate Chemical compound [O-]C(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-M 0.000 claims description 21
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 239000004094 surface-active agent Substances 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 241000244206 Nematoda Species 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 241000239223 Arachnida Species 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 230000036541 health Effects 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 239000013598 vector Substances 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 4
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 4
• 238000002405 diagnostic procedure Methods 0.000 claims description 4
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 3
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• ZMLHBBXPXZXTSP-UHFFFAOYSA-N 2-fluoropropane Chemical group C[C](C)F ZMLHBBXPXZXTSP-UHFFFAOYSA-N 0.000 claims description 3
• 239000004606 Fillers/Extenders Substances 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
• 125000004432 carbon atom Chemical group C* 0.000 description 49
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
• 238000002360 preparation method Methods 0.000 description 46
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• 239000002904 solvent Substances 0.000 description 41
• 239000000243 solution Substances 0.000 description 40
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• 239000003112 inhibitor Substances 0.000 description 36
• 150000003254 radicals Chemical class 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
• 229920000742 Cotton Polymers 0.000 description 31
• 241000219146 Gossypium Species 0.000 description 31
• 102000004169 proteins and genes Human genes 0.000 description 29
• 239000007787 solid Substances 0.000 description 28
• 238000011282 treatment Methods 0.000 description 28
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 27
• 235000009973 maize Nutrition 0.000 description 27
• 235000018102 proteins Nutrition 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 238000002156 mixing Methods 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 230000015572 biosynthetic process Effects 0.000 description 19
• 230000009261 transgenic effect Effects 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
• 235000019439 ethyl acetate Nutrition 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 16
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
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• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 10
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
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• 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 9
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• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
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