JP5571062B2 - 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 - Google Patents
殺真菌剤ヒドロキシモイル−テトラゾール誘導体 Download PDFInfo
- Publication number
- JP5571062B2 JP5571062B2 JP2011500217A JP2011500217A JP5571062B2 JP 5571062 B2 JP5571062 B2 JP 5571062B2 JP 2011500217 A JP2011500217 A JP 2011500217A JP 2011500217 A JP2011500217 A JP 2011500217A JP 5571062 B2 JP5571062 B2 JP 5571062B2
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- methyl
- mmol
- alkyl
- 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.)
- Expired - Fee Related
Links
- 239000000417 fungicide Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 166
- 238000000034 method Methods 0.000 claims description 145
- 125000005843 halogen group Chemical group 0.000 claims description 136
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 241000233866 Fungi Species 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 230000003032 phytopathogenic effect Effects 0.000 claims description 11
- 235000013399 edible fruits Nutrition 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 4
- 239000012872 agrochemical composition Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000007654 immersion Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 187
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 173
- -1 tetrazolyl oxime Chemical class 0.000 description 148
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 114
- 201000010099 disease Diseases 0.000 description 113
- 238000002360 preparation method Methods 0.000 description 93
- 230000008569 process Effects 0.000 description 87
- 238000006243 chemical reaction Methods 0.000 description 81
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 80
- 235000019253 formic acid Nutrition 0.000 description 77
- 239000000243 solution Substances 0.000 description 77
- 238000004128 high performance liquid chromatography Methods 0.000 description 76
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 65
- 239000003921 oil Substances 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 239000000741 silica gel Substances 0.000 description 52
- 229910002027 silica gel Inorganic materials 0.000 description 52
- 108090000623 proteins and genes Proteins 0.000 description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 37
- 239000012044 organic layer Substances 0.000 description 36
- 239000007787 solid Substances 0.000 description 36
- 239000002904 solvent Substances 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- 238000004587 chromatography analysis Methods 0.000 description 29
- 102000004169 proteins and genes Human genes 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- 229910002091 carbon monoxide Inorganic materials 0.000 description 23
- 239000010410 layer Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 16
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 16
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 16
- 235000005822 corn Nutrition 0.000 description 16
- 230000000749 insecticidal effect Effects 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 230000009261 transgenic effect Effects 0.000 description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 description 10
- 230000014509 gene expression Effects 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- 150000002923 oximes Chemical class 0.000 description 10
- 241000193388 Bacillus thuringiensis Species 0.000 description 9
- 229940097012 bacillus thuringiensis Drugs 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
- 230000002068 genetic effect Effects 0.000 description 9
- 230000035882 stress Effects 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
- 230000035772 mutation Effects 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 7
- 240000002024 Gossypium herbaceum Species 0.000 description 7
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000000855 fungicidal effect Effects 0.000 description 7
- 238000010353 genetic engineering Methods 0.000 description 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- PKZVTOZGYYQQJH-UHFFFAOYSA-N n-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(Br)=N1 PKZVTOZGYYQQJH-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 7
- 239000002023 wood Substances 0.000 description 7
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 6
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 101710151559 Crystal protein Proteins 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 239000005562 Glyphosate Substances 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- SNWXPJCGFXFPNB-UHFFFAOYSA-N N-[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]hydroxylamine Chemical compound CSC1=CC=CC(C(=NO)C=2N(N=NN=2)C)=C1 SNWXPJCGFXFPNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 108700019146 Transgenes Proteins 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 6
- 229940097068 glyphosate Drugs 0.000 description 6
- 150000002466 imines Chemical class 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 5
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 5
- 108010000700 Acetolactate synthase Proteins 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000223218 Fusarium Species 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 206010021929 Infertility male Diseases 0.000 description 5
- 208000007466 Male Infertility Diseases 0.000 description 5
- 241000228453 Pyrenophora Species 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- NPTDXPDGUHAFKC-UHFFFAOYSA-N ethynylcyclopropane Chemical group C#CC1CC1 NPTDXPDGUHAFKC-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 5
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 5
- NWWAXJGQMXAMCY-UHFFFAOYSA-N n-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CSC(Br)=N1 NWWAXJGQMXAMCY-UHFFFAOYSA-N 0.000 description 5
- BKZSAFCOQMIUIC-UHFFFAOYSA-N n-[[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(C2OCCO2)=N1 BKZSAFCOQMIUIC-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000000069 prophylactic effect Effects 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
- PUUHOIJJZAGFNK-UHFFFAOYSA-N 2-bromo-4-(bromomethyl)-1,3-thiazole Chemical compound BrCC1=CSC(Br)=N1 PUUHOIJJZAGFNK-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 241000228212 Aspergillus Species 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 241000131448 Mycosphaerella Species 0.000 description 4
- VJIOPMFAABGXNA-UHFFFAOYSA-N N-[(1-methyltetrazol-5-yl)-phenylmethylidene]hydroxylamine Chemical compound CN1N=NN=C1C(=NO)C1=CC=CC=C1 VJIOPMFAABGXNA-UHFFFAOYSA-N 0.000 description 4
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 4
- XKCVUHDUKJJUQP-UHFFFAOYSA-N N-[[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]methylidene]hydroxylamine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(C=NO)=N1 XKCVUHDUKJJUQP-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 239000012973 diazabicyclooctane Substances 0.000 description 4
- WHOBZBLBTZHMGY-UHFFFAOYSA-N ditert-butyl(ethyl)phosphane Chemical compound CCP(C(C)(C)C)C(C)(C)C WHOBZBLBTZHMGY-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 150000002940 palladium Chemical class 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- RGGBSQPGJZUNNX-UHFFFAOYSA-N tert-butyl n-(2-cyclohexylethyl)-n-[6-(hydroxymethyl)pyridin-2-yl]carbamate Chemical compound C=1C=CC(CO)=NC=1N(C(=O)OC(C)(C)C)CCC1CCCCC1 RGGBSQPGJZUNNX-UHFFFAOYSA-N 0.000 description 4
- WZDMEUOIVUZTPB-UHFFFAOYSA-N tert-butyl n-(6-bromopyridin-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(Br)=N1 WZDMEUOIVUZTPB-UHFFFAOYSA-N 0.000 description 4
- BNLOFXUVYJUBJM-UHFFFAOYSA-N tert-butyl n-(6-formylpyridin-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(C=O)=N1 BNLOFXUVYJUBJM-UHFFFAOYSA-N 0.000 description 4
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- WGIXWCYGUXJNEK-UHFFFAOYSA-N 1-(1-methyltetrazol-5-yl)-n-[(6-pentylsulfanylpyridin-2-yl)methoxy]-1-phenylmethanimine Chemical compound CCCCCSC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 WGIXWCYGUXJNEK-UHFFFAOYSA-N 0.000 description 3
- MAZMJMLUKYPLEI-UHFFFAOYSA-N 2,2-dimethyl-n-(6-methylpyridin-2-yl)propanamide Chemical compound CC1=CC=CC(NC(=O)C(C)(C)C)=N1 MAZMJMLUKYPLEI-UHFFFAOYSA-N 0.000 description 3
- JRQAAYVLPPGEHT-UHFFFAOYSA-N 2-bromoethylcyclohexane Chemical compound BrCCC1CCCCC1 JRQAAYVLPPGEHT-UHFFFAOYSA-N 0.000 description 3
- OXPQMVYZUANSRR-UHFFFAOYSA-N 3-(dimethylamino)-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC(N(C)C)=C1 OXPQMVYZUANSRR-UHFFFAOYSA-N 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHVCQLLCFQUCPC-UHFFFAOYSA-N 6-[[[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CSC1=CC=CC(C(=NOCC=2N=C(N)C=CC=2)C=2N(N=NN=2)C)=C1 UHVCQLLCFQUCPC-UHFFFAOYSA-N 0.000 description 3
- AUBAFPZVFLTWNE-UHFFFAOYSA-N 6-bromo-2-(bromomethyl)-3-fluoropyridine Chemical compound FC1=CC=C(Br)N=C1CBr AUBAFPZVFLTWNE-UHFFFAOYSA-N 0.000 description 3
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 3
- 241000223600 Alternaria Species 0.000 description 3
- 241000228197 Aspergillus flavus Species 0.000 description 3
- 241000193755 Bacillus cereus Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000222290 Cladosporium Species 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000400611 Eucalyptus deanei Species 0.000 description 3
- 241001459558 Monographella nivalis Species 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- LYERGOAWGVREBL-UHFFFAOYSA-N N-[[3-(dimethylamino)phenyl]-(1-methyltetrazol-5-yl)methylidene]hydroxylamine Chemical compound CN(C)C1=CC=CC(C(=NO)C=2N(N=NN=2)C)=C1 LYERGOAWGVREBL-UHFFFAOYSA-N 0.000 description 3
- 241001361634 Rhizoctonia Species 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- 241001533598 Septoria Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- PRCODZYNNJSFMR-UHFFFAOYSA-N [6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]methanamine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(CN)=N1 PRCODZYNNJSFMR-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 230000001488 breeding effect Effects 0.000 description 3
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 3
- 239000001639 calcium acetate Substances 0.000 description 3
- 235000011092 calcium acetate Nutrition 0.000 description 3
- 229960005147 calcium acetate Drugs 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000035558 fertility Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- WJDONERCJCNCPI-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)formamide Chemical compound CC1=CC=CC(NC=O)=N1 WJDONERCJCNCPI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OZPKEYDTBZKJDM-UHFFFAOYSA-N n-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyltetrazol-1-yl)-1-phenylmethanimine Chemical compound CC1=NN=NN1C(C=1C=CC=CC=1)=NOCC1=CSC(Br)=N1 OZPKEYDTBZKJDM-UHFFFAOYSA-N 0.000 description 3
- UQPMRYXCQSYBBP-UHFFFAOYSA-N n-[(5-methyltetrazol-1-yl)-phenylmethylidene]hydroxylamine Chemical compound CC1=NN=NN1C(=NO)C1=CC=CC=C1 UQPMRYXCQSYBBP-UHFFFAOYSA-N 0.000 description 3
- GBEUHZMLBJUQMY-UHFFFAOYSA-N n-[(6-bromo-3-fluoropyridin-2-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=NC(Br)=CC=C1F GBEUHZMLBJUQMY-UHFFFAOYSA-N 0.000 description 3
- ICZXSVCIHPXIFS-UHFFFAOYSA-N n-[(6-bromo-5-methoxypyridin-2-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound N1=C(Br)C(OC)=CC=C1CON=C(C=1C=CC=CC=1)C1=NN=NN1C ICZXSVCIHPXIFS-UHFFFAOYSA-N 0.000 description 3
- ZBQCWVDMRUHIDC-UHFFFAOYSA-N n-[[6-(cyclohexyloxyiminomethyl)pyridin-2-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(C=NOC2CCCCC2)=N1 ZBQCWVDMRUHIDC-UHFFFAOYSA-N 0.000 description 3
- SVOHGGRMRWEUSR-UHFFFAOYSA-N n-hexyl-n-(6-methylpyridin-2-yl)formamide Chemical compound CCCCCCN(C=O)C1=CC=CC(C)=N1 SVOHGGRMRWEUSR-UHFFFAOYSA-N 0.000 description 3
- OLUVHIOXLODFLH-UHFFFAOYSA-N n-methoxy-n-methyl-3-methylsulfanylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC(SC)=C1 OLUVHIOXLODFLH-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- XVFGPRRJODWLES-UHFFFAOYSA-N tert-butyl n-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]-n-pentoxycarbamate Chemical compound CCCCCON(C(=O)OC(C)(C)C)C1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 XVFGPRRJODWLES-UHFFFAOYSA-N 0.000 description 3
- FCGXFFFASXKEHS-UHFFFAOYSA-N tert-butyl n-pentoxycarbamate Chemical compound CCCCCONC(=O)OC(C)(C)C FCGXFFFASXKEHS-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000001131 transforming effect Effects 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- MQMFHTSXMPGVBI-UHFFFAOYSA-N (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol Chemical compound CC=1SC(Br)=NC=1CO MQMFHTSXMPGVBI-UHFFFAOYSA-N 0.000 description 2
- SXIOKAVUZIHCDD-UHFFFAOYSA-N (6-bromo-3-fluoropyridin-2-yl)methanol Chemical compound OCC1=NC(Br)=CC=C1F SXIOKAVUZIHCDD-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 2
- WEWOTHRAXCRSBK-UHFFFAOYSA-N 1-(1-methyltetrazol-5-yl)-1-phenyl-n-[(6-phenylpyridin-2-yl)methoxy]methanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(C=2C=CC=CC=2)=N1 WEWOTHRAXCRSBK-UHFFFAOYSA-N 0.000 description 2
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 2
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- VLSRYYBTRSYZDF-UHFFFAOYSA-M 2-(1,3-dioxolan-2-yl)-6-(pyridin-1-ium-1-ylmethyl)pyridine;bromide;hydrobromide Chemical compound Br.[Br-].C=1C=CC=C[N+]=1CC(N=1)=CC=CC=1C1OCCO1 VLSRYYBTRSYZDF-UHFFFAOYSA-M 0.000 description 2
- CFKHXBFNPRUFKZ-UHFFFAOYSA-N 2-[6-(bromomethyl)pyridin-2-yl]isoindole-1,3-dione Chemical compound BrCC1=CC=CC(N2C(C3=CC=CC=C3C2=O)=O)=N1 CFKHXBFNPRUFKZ-UHFFFAOYSA-N 0.000 description 2
- TUIUWOKXRRHHPA-UHFFFAOYSA-N 2-[[6-(chloromethyl)pyridin-2-yl]methyl]isoindole-1,3-dione Chemical compound ClCC1=CC=CC(CN2C(C3=CC=CC=C3C2=O)=O)=N1 TUIUWOKXRRHHPA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SQSBWYSRKYKNGH-UHFFFAOYSA-N 2-bromo-4-(bromomethyl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(Br)=NC=1CBr SQSBWYSRKYKNGH-UHFFFAOYSA-N 0.000 description 2
- NBQFZJVTVGZJRO-UHFFFAOYSA-N 4-[[[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]-1,3-thiazol-2-amine Chemical compound CSC1=CC=CC(C(=NOCC=2N=C(N)SC=2)C=2N(N=NN=2)C)=C1 NBQFZJVTVGZJRO-UHFFFAOYSA-N 0.000 description 2
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- KGAUXVJHJAMVQS-UHFFFAOYSA-N 6-[[[[3-(dimethylamino)phenyl]-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CN(C)C1=CC=CC(C(=NOCC=2N=C(N)C=CC=2)C=2N(N=NN=2)C)=C1 KGAUXVJHJAMVQS-UHFFFAOYSA-N 0.000 description 2
- PSNKSEHKWXMETD-UHFFFAOYSA-N 6-bromo-3-fluoro-2-methyl-1-oxidopyridin-1-ium Chemical compound CC1=C(F)C=CC(Br)=[N+]1[O-] PSNKSEHKWXMETD-UHFFFAOYSA-N 0.000 description 2
- BKLJUYPLUWUEOQ-UHFFFAOYSA-N 6-bromopyridin-2-amine Chemical compound NC1=CC=CC(Br)=N1 BKLJUYPLUWUEOQ-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229920000856 Amylose Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241001444083 Aphanomyces Species 0.000 description 2
- 241000208838 Asteraceae Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000190150 Bipolaris sorokiniana Species 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219193 Brassicaceae Species 0.000 description 2
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000222199 Colletotrichum Species 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 241001529717 Corticium <basidiomycota> Species 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 102000016680 Dioxygenases Human genes 0.000 description 2
- 108010028143 Dioxygenases Proteins 0.000 description 2
- 241000125117 Elsinoe Species 0.000 description 2
- 241000223194 Fusarium culmorum Species 0.000 description 2
- 241000223195 Fusarium graminearum Species 0.000 description 2
- 241000461774 Gloeosporium Species 0.000 description 2
- 241001620302 Glomerella <beetle> Species 0.000 description 2
- 229920001503 Glucan Polymers 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 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 2
- 241000228456 Leptosphaeria Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 241000005782 Monographella 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
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 241001123663 Penicillium expansum Species 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 2
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 2
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- 241000918584 Pythium ultimum Species 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- 241000220222 Rosaceae Species 0.000 description 2
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 108090000992 Transferases Proteins 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 2
- TVUMEDJRIMXGPE-UHFFFAOYSA-N [6-(1,3-dioxolan-2-yl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(C2OCCO2)=N1 TVUMEDJRIMXGPE-UHFFFAOYSA-N 0.000 description 2
- INFJVQOJQGSHAW-UHFFFAOYSA-N [6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]methanol Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(CO)=N1 INFJVQOJQGSHAW-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012190 activator Chemical group 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000001602 bicycloalkyls Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010367 cloning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- HGTBZFMPHBAUCQ-KHZPMNTOSA-N cyclopentane;dicyclohexyl-[(1r)-1-(2-diphenylphosphanylcyclopentyl)ethyl]phosphane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.[C]1([C@@H](C)P(C2CCCCC2)C2CCCCC2)[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 HGTBZFMPHBAUCQ-KHZPMNTOSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000009368 gene silencing by RNA Effects 0.000 description 2
- 235000003869 genetically modified organism Nutrition 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 2
- HUDHQMNQKJPEBG-UHFFFAOYSA-N n-(2-cyclohexylethyl)-6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(NCCC2CCCCC2)=N1 HUDHQMNQKJPEBG-UHFFFAOYSA-N 0.000 description 2
- APSBAPSKJULCEK-UHFFFAOYSA-N n-[(2,5-dichloro-1,3-thiazol-4-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=C(Cl)SC(Cl)=N1 APSBAPSKJULCEK-UHFFFAOYSA-N 0.000 description 2
- GPSIUZZEDHDGQI-UHFFFAOYSA-N n-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(3-methylsulfanylphenyl)-1-(1-methyltetrazol-5-yl)methanimine Chemical compound CSC1=CC=CC(C(=NOCC=2N=C(Br)SC=2)C=2N(N=NN=2)C)=C1 GPSIUZZEDHDGQI-UHFFFAOYSA-N 0.000 description 2
- NNINDPLMALRVDR-UHFFFAOYSA-N n-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound S1C(Br)=NC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=C1C NNINDPLMALRVDR-UHFFFAOYSA-N 0.000 description 2
- BCWDHUHBSMCNNN-UHFFFAOYSA-N n-hexyl-6-[[[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CCCCCCNC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=C(SC)C=CC=2)=N1 BCWDHUHBSMCNNN-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000010451 perlite Substances 0.000 description 2
- 235000019362 perlite Nutrition 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 108010082527 phosphinothricin N-acetyltransferase Proteins 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- MJZMLBVNMBLKQY-UHFFFAOYSA-N sulfonylphosphane Chemical compound O=S(=O)=P MJZMLBVNMBLKQY-UHFFFAOYSA-N 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- RCLIUAJKGDHJMP-UHFFFAOYSA-N tert-butyl n-[6-(hydroxymethyl)pyridin-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(CO)=N1 RCLIUAJKGDHJMP-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- MOCLKAIEXMXITN-UHFFFAOYSA-N (3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methanone Chemical compound CSC1=CC=CC(C(=O)C=2N(N=NN=2)C)=C1 MOCLKAIEXMXITN-UHFFFAOYSA-N 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WMIBOXVGNASTKN-UHFFFAOYSA-N 1-[[4-(chloromethyl)-1,3-thiazol-2-yl]amino]propan-2-one Chemical compound CC(=O)CNC1=NC(CCl)=CS1 WMIBOXVGNASTKN-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- PRULVQBZCDYZCN-UHFFFAOYSA-N 2,5-dichloro-4-(chloromethyl)-1,3-thiazole Chemical compound ClCC=1N=C(Cl)SC=1Cl PRULVQBZCDYZCN-UHFFFAOYSA-N 0.000 description 1
- IWQNFYRJSVJWQA-UHFFFAOYSA-N 2,6-bis(chloromethyl)pyridine Chemical compound ClCC1=CC=CC(CCl)=N1 IWQNFYRJSVJWQA-UHFFFAOYSA-N 0.000 description 1
- BRLNLMMLCNZBNP-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-6-methylpyridine Chemical compound CC1=CC=CC(C2OCCO2)=N1 BRLNLMMLCNZBNP-UHFFFAOYSA-N 0.000 description 1
- CGAFUFBOSYRKOT-UHFFFAOYSA-N 2-[6-[[[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-yl]isoindole-1,3-dione Chemical compound CSC1=CC=CC(C(=NOCC=2N=C(C=CC=2)N2C(C3=CC=CC=C3C2=O)=O)C=2N(N=NN=2)C)=C1 CGAFUFBOSYRKOT-UHFFFAOYSA-N 0.000 description 1
- ZEJHNDPZVBTFCC-UHFFFAOYSA-N 2-[6-[[[[3-(dimethylamino)phenyl]-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-yl]isoindole-1,3-dione Chemical compound CN(C)C1=CC=CC(C(=NOCC=2N=C(C=CC=2)N2C(C3=CC=CC=C3C2=O)=O)C=2N(N=NN=2)C)=C1 ZEJHNDPZVBTFCC-UHFFFAOYSA-N 0.000 description 1
- DIUSGLJJHQEDSK-UHFFFAOYSA-N 2-[[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]methyl]isoindole-1,3-dione Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(CN2C(C3=CC=CC=C3C2=O)=O)=N1 DIUSGLJJHQEDSK-UHFFFAOYSA-N 0.000 description 1
- LFIHYCFTNHIAQQ-UHFFFAOYSA-N 2-bromo-6-(bromomethyl)-3-methoxypyridine Chemical compound COC1=CC=C(CBr)N=C1Br LFIHYCFTNHIAQQ-UHFFFAOYSA-N 0.000 description 1
- LSRDTCMNGSMEEI-UHFFFAOYSA-N 2-bromo-6-(bromomethyl)pyridine Chemical compound BrCC1=CC=CC(Br)=N1 LSRDTCMNGSMEEI-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- LAUKAWOMRTYHJK-UHFFFAOYSA-N 2-pyrimidin-2-yloxysulfanylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1SOC1=NC=CC=N1 LAUKAWOMRTYHJK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- KKADPXVIOXHVKN-UHFFFAOYSA-M 3-(4-hydroxyphenyl)pyruvate Chemical compound OC1=CC=C(CC(=O)C([O-])=O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-M 0.000 description 1
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 1
- MJGGYRQWXSPWFK-UHFFFAOYSA-N 3-[n-[(2-bromo-1,3-thiazol-4-yl)methoxy]-c-(1-methyltetrazol-5-yl)carbonimidoyl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(C(=NOCC=2N=C(Br)SC=2)C=2N(N=NN=2)C)=C1 MJGGYRQWXSPWFK-UHFFFAOYSA-N 0.000 description 1
- PZGADOOBMVLBJE-UHFFFAOYSA-N 3-methylsulfanylbenzoic acid Chemical compound CSC1=CC=CC(C(O)=O)=C1 PZGADOOBMVLBJE-UHFFFAOYSA-N 0.000 description 1
- RJNUXEDAPIKMDE-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride;hydrate Chemical compound O.[Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 RJNUXEDAPIKMDE-UHFFFAOYSA-M 0.000 description 1
- QYKUGBMFPFOPNE-UHFFFAOYSA-N 4-(chloromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC(CCl)=CS1 QYKUGBMFPFOPNE-UHFFFAOYSA-N 0.000 description 1
- YSYILILRFKOSMG-UHFFFAOYSA-N 4-(chloromethyl)-n-methyl-1,3-thiazol-2-amine Chemical compound CNC1=NC(CCl)=CS1 YSYILILRFKOSMG-UHFFFAOYSA-N 0.000 description 1
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
- FYLGONVKZPRGMC-UHFFFAOYSA-N 4-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]-1,3-thiazol-2-amine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CSC(N)=N1 FYLGONVKZPRGMC-UHFFFAOYSA-N 0.000 description 1
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 description 1
- PRZRAMLXTKZUHF-UHFFFAOYSA-N 5-oxo-n-sulfonyl-4h-triazole-1-carboxamide Chemical compound O=S(=O)=NC(=O)N1N=NCC1=O PRZRAMLXTKZUHF-UHFFFAOYSA-N 0.000 description 1
- BAVDPOWLMDIGKH-UHFFFAOYSA-N 6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]-n-pentoxypyridin-2-amine Chemical compound CCCCCONC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 BAVDPOWLMDIGKH-UHFFFAOYSA-N 0.000 description 1
- HEHFKZSTTDBTLE-UHFFFAOYSA-N 6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(N)=N1 HEHFKZSTTDBTLE-UHFFFAOYSA-N 0.000 description 1
- CTRARPNXIJSBCH-UHFFFAOYSA-N 6-[[[[3-(dimethylamino)phenyl]-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]-n-(3-phenylpropyl)pyridin-2-amine Chemical compound CN(C)C1=CC=CC(C(=NOCC=2N=C(NCCCC=3C=CC=CC=3)C=CC=2)C=2N(N=NN=2)C)=C1 CTRARPNXIJSBCH-UHFFFAOYSA-N 0.000 description 1
- BFQONZCQHGIKIY-UHFFFAOYSA-N 6-bromo-3-fluoro-2-methylpyridine Chemical compound CC1=NC(Br)=CC=C1F BFQONZCQHGIKIY-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000349731 Afzelia bipindensis Species 0.000 description 1
- 241000589159 Agrobacterium sp. Species 0.000 description 1
- 241001157812 Alternaria brassicicola Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 241000208223 Anacardiaceae Species 0.000 description 1
- 241000208173 Apiaceae Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241001167018 Aroa Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- BHELIUBJHYAEDK-OAIUPTLZSA-N Aspoxicillin Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3[C@H](C(C)(C)S[C@@H]32)C(O)=O)=O)NC(=O)[C@H](N)CC(=O)NC)=CC=C(O)C=C1 BHELIUBJHYAEDK-OAIUPTLZSA-N 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 108010016529 Bacillus amyloliquefaciens ribonuclease Proteins 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001465178 Bipolaris Species 0.000 description 1
- 241001480060 Blumeria Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- JTOZRNOTEKMIGS-UHFFFAOYSA-N BrC1=CC=C(C(=[N+]1[O-])C)F.CO Chemical compound BrC1=CC=C(C(=[N+]1[O-])C)F.CO JTOZRNOTEKMIGS-UHFFFAOYSA-N 0.000 description 1
- HFRAMPLCMQTYBM-UHFFFAOYSA-N BrC=1SC(=C(N1)C(=O)OC)C.BrC=1SC(=C(N1)CO)C Chemical compound BrC=1SC(=C(N1)C(=O)OC)C.BrC=1SC(=C(N1)CO)C HFRAMPLCMQTYBM-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 241000220243 Brassica sp. Species 0.000 description 1
- 241000233684 Bremia Species 0.000 description 1
- 241000233685 Bremia lactucae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GEGMVYRPIVZCGA-UHFFFAOYSA-N C(N)(OC1=NC(=CC=C1)CON=C(C1=CC=CC=C1)C1=NN=NN1C)=S Chemical compound C(N)(OC1=NC(=CC=C1)CON=C(C1=CC=CC=C1)C1=NN=NN1C)=S GEGMVYRPIVZCGA-UHFFFAOYSA-N 0.000 description 1
- FCJFHVDLMZPBFO-UHFFFAOYSA-N CC1=NN=NN1C(=N)C1=CC=CC=C1 Chemical compound CC1=NN=NN1C(=N)C1=CC=CC=C1 FCJFHVDLMZPBFO-UHFFFAOYSA-N 0.000 description 1
- XBMRWQWMMIYMLY-UHFFFAOYSA-N CN(C)C.C(CCC)N Chemical compound CN(C)C.C(CCC)N XBMRWQWMMIYMLY-UHFFFAOYSA-N 0.000 description 1
- JVWKTNMCRGYFLY-UHFFFAOYSA-N CN1N=NN=C1.CN(C=1C=C(C=CC1)C(=O)C1=NN=NN1C)C Chemical compound CN1N=NN=C1.CN(C=1C=C(C=CC1)C(=O)C1=NN=NN1C)C JVWKTNMCRGYFLY-UHFFFAOYSA-N 0.000 description 1
- NALCPSPDDNPOIV-UHFFFAOYSA-N CN1N=NN=C1.CSC=1C=C(C=CC1)C(=O)C1=NN=NN1C Chemical compound CN1N=NN=C1.CSC=1C=C(C=CC1)C(=O)C1=NN=NN1C NALCPSPDDNPOIV-UHFFFAOYSA-N 0.000 description 1
- XTYVCAHADNHDPI-UHFFFAOYSA-N CSC=1C=C(C=CC1)C(C1=NN=NN1C)=NOCC1=CC=CC(=N1)N1CC2=CC=CC=C2C1 Chemical compound CSC=1C=C(C=CC1)C(C1=NN=NN1C)=NOCC1=CC=CC(=N1)N1CC2=CC=CC=C2C1 XTYVCAHADNHDPI-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 240000001817 Cereus hexagonus Species 0.000 description 1
- 108700040089 Chitin synthases Proteins 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241001149955 Cladosporium cladosporioides Species 0.000 description 1
- 241001149956 Cladosporium herbarum Species 0.000 description 1
- 241000221751 Claviceps purpurea Species 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 108091026890 Coding region Proteins 0.000 description 1
- 241001123534 Colletotrichum coccodes Species 0.000 description 1
- 241001120669 Colletotrichum lindemuthianum Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001508802 Diaporthe Species 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 101000999829 Escherichia coli (strain K12) NH(3)-dependent NAD(+) synthetase Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000221997 Exobasidium Species 0.000 description 1
- 241001661371 Exobasidium vexans Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000414044 Fomitiporia Species 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000222336 Ganoderma Species 0.000 description 1
- 241000401653 Ganoderma orbiforme Species 0.000 description 1
- 241000223247 Gloeocercospora Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 241000555709 Guignardia Species 0.000 description 1
- 241000221557 Gymnosporangium Species 0.000 description 1
- 241001409809 Gymnosporangium sabinae Species 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000342321 Hyaloperonospora brassicae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000758791 Juglandaceae Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241001293495 Lactuca virosa Species 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 241000228457 Leptosphaeria maculans Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241001495424 Macrophomina Species 0.000 description 1
- 241001495426 Macrophomina phaseolina Species 0.000 description 1
- 241001344133 Magnaporthe Species 0.000 description 1
- 241001344131 Magnaporthe grisea Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 101000763602 Manilkara zapota Thaumatin-like protein 1 Proteins 0.000 description 1
- 101000763586 Manilkara zapota Thaumatin-like protein 1a Proteins 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 241001668538 Mollisia Species 0.000 description 1
- 241001518729 Monilinia Species 0.000 description 1
- 241000862466 Monilinia laxa Species 0.000 description 1
- 101000966653 Musa acuminata Glucan endo-1,3-beta-glucosidase Proteins 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- ZZARPEOYHWUIDS-UHFFFAOYSA-N NC=1SC(=C(N1)C(=O)OC)C.BrC=1SC(=C(N1)C(=O)OC)C Chemical compound NC=1SC(=C(N1)C(=O)OC)C.BrC=1SC(=C(N1)C(=O)OC)C ZZARPEOYHWUIDS-UHFFFAOYSA-N 0.000 description 1
- 241000379990 Nakataea oryzae Species 0.000 description 1
- 241001226034 Nectria <echinoderm> Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000556984 Neonectria galligena Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108010019703 Nicotinamidase Proteins 0.000 description 1
- 102000000780 Nicotinate phosphoribosyltransferase Human genes 0.000 description 1
- 108700040046 Nicotinate phosphoribosyltransferases Proteins 0.000 description 1
- 241000998584 Nuda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WWTYNSYRXHPDDX-UHFFFAOYSA-N O1C(OCC1)C1=NC(=CC=C1)C.O1C(OCC1)C1=[N+](C(=CC=C1)C)[O-] Chemical compound O1C(OCC1)C1=NC(=CC=C1)C.O1C(OCC1)C1=[N+](C(=CC=C1)C)[O-] WWTYNSYRXHPDDX-UHFFFAOYSA-N 0.000 description 1
- KNLSODFDXPSRRC-UHFFFAOYSA-N O1C(OCC1)C1=[N+](C(=CC=C1)C)[O-].O1C(OCC1)C1=CC=CC(=N1)CO Chemical compound O1C(OCC1)C1=[N+](C(=CC=C1)C)[O-].O1C(OCC1)C1=CC=CC(=N1)CO KNLSODFDXPSRRC-UHFFFAOYSA-N 0.000 description 1
- ISOVVFXHNUFPJJ-UHFFFAOYSA-N ON=C(C1=CC=CC=C1)C1=NN=NN1C.O1C(OCC1)C1=CC=CC(=N1)CON=C(C1=CC=CC=C1)C1=NN=NN1C Chemical compound ON=C(C1=CC=CC=C1)C1=NN=NN1C.O1C(OCC1)C1=CC=CC(=N1)CON=C(C1=CC=CC=C1)C1=NN=NN1C ISOVVFXHNUFPJJ-UHFFFAOYSA-N 0.000 description 1
- 241000144610 Oculimacula acuformis Species 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 240000000267 Pandorea jasminoides Species 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000201565 Peronospora viciae f. sp. pisi Species 0.000 description 1
- 240000007377 Petunia x hybrida Species 0.000 description 1
- 241000263269 Phaeoacremonium minimum Species 0.000 description 1
- 241000047848 Phaeomoniella Species 0.000 description 1
- 241000555275 Phaeosphaeria Species 0.000 description 1
- 241000440444 Phakopsora Species 0.000 description 1
- 241000682645 Phakopsora pachyrhizi Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000210649 Phyllosticta ampelicida Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000896242 Podosphaera Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 238000006972 Polonovski rearrangement reaction Methods 0.000 description 1
- 108010035004 Prephenate Dehydrogenase Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000589516 Pseudomonas 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
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 241000918585 Pythium aphanidermatum Species 0.000 description 1
- 238000012228 RNA interference-mediated gene silencing Methods 0.000 description 1
- 108091030071 RNAI Proteins 0.000 description 1
- 241000173769 Ramularia collo-cygni Species 0.000 description 1
- 241000196686 Ramulariopsis gossypii Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 241001515790 Rhynchosporium secalis Species 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 241001619450 Rigidoporus Species 0.000 description 1
- 241001638069 Rigidoporus microporus Species 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 241001093501 Rutaceae Species 0.000 description 1
- CUVBLOWIKATMQJ-UHFFFAOYSA-M S(=O)(Br)Br.Br.[Br-].O1C(OCC1)C1=CC=CC(=N1)C[N+]1=CC=CC=C1 Chemical compound S(=O)(Br)Br.Br.[Br-].O1C(OCC1)C1=CC=CC(=N1)C[N+]1=CC=CC=C1 CUVBLOWIKATMQJ-UHFFFAOYSA-M 0.000 description 1
- SAFDCMKMJBKZEI-UHFFFAOYSA-N S(=O)(Br)Br.BrC=1SC(=C(N1)CBr)C Chemical compound S(=O)(Br)Br.BrC=1SC(=C(N1)CBr)C SAFDCMKMJBKZEI-UHFFFAOYSA-N 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000800293 Sarocladium Species 0.000 description 1
- 241000800294 Sarocladium oryzae Species 0.000 description 1
- 244000007853 Sarothamnus scoparius Species 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241001533580 Septoria lycopersici Species 0.000 description 1
- 101710084578 Short neurotoxin 1 Proteins 0.000 description 1
- 241001291279 Solanum galapagense Species 0.000 description 1
- 241000011575 Spilocaea Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 108010043934 Sucrose synthase Proteins 0.000 description 1
- 108700006291 Sucrose-phosphate synthases Proteins 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001540751 Talaromyces ruber Species 0.000 description 1
- 241000228446 Taphrina Species 0.000 description 1
- 241000228448 Taphrina deformans Species 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 101710182532 Toxin a Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- 235000019714 Triticale Nutrition 0.000 description 1
- 241000333201 Typhula incarnata Species 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- 241001154828 Urocystis <tapeworm> Species 0.000 description 1
- 241000157667 Urocystis occulta Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 241000905623 Venturia oleaginea Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 241000726445 Viroids Species 0.000 description 1
- 241000219094 Vitaceae Species 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
- 229920002522 Wood fibre Polymers 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000589636 Xanthomonas campestris Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- FBRJOMMIILHLCG-VOTSOKGWSA-N [(e)-2-cyclohexylethenyl]boronic acid Chemical compound OB(O)\C=C\C1CCCCC1 FBRJOMMIILHLCG-VOTSOKGWSA-N 0.000 description 1
- GWFKSQSXNUNYAC-AATRIKPKSA-N [(e)-hex-1-enyl]boronic acid Chemical compound CCCC\C=C\B(O)O GWFKSQSXNUNYAC-AATRIKPKSA-N 0.000 description 1
- DCLOBAGBVMUMCA-UHFFFAOYSA-N [3-(dimethylamino)phenyl]-(1-methyltetrazol-5-yl)methanone Chemical compound CN(C)C1=CC=CC(C(=O)C=2N(N=NN=2)C)=C1 DCLOBAGBVMUMCA-UHFFFAOYSA-N 0.000 description 1
- KSQLHMRSEZCVDV-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl] carbamate Chemical compound NC(=O)OC1=CC=CC(CO)=N1 KSQLHMRSEZCVDV-UHFFFAOYSA-N 0.000 description 1
- 230000036579 abiotic stress Effects 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 108020002494 acetyltransferase Proteins 0.000 description 1
- 102000005421 acetyltransferase Human genes 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 238000007083 alkoxycarbonylation reaction Methods 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000433 anti-nutritional effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 108010040093 cellulose synthase Proteins 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 210000003763 chloroplast Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HGTBZFMPHBAUCQ-WLOLSGMKSA-N cyclopentane;dicyclohexyl-[(1s)-1-(2-diphenylphosphanylcyclopentyl)ethyl]phosphane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.[C]1([C@H](C)P(C2CCCCC2)C2CCCCC2)[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 HGTBZFMPHBAUCQ-WLOLSGMKSA-N 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000023753 dehiscence Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QGBQGMHXBSLYLZ-UHFFFAOYSA-N ditert-butyl-(1-naphthalen-1-ylnaphthalen-2-yl)phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3P(C(C)(C)C)C(C)(C)C)=CC=CC2=C1 QGBQGMHXBSLYLZ-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 235000021038 drupes Nutrition 0.000 description 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IDHNOWGENVCVSX-UHFFFAOYSA-N ethyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC=CC=C1NC(=O)OC(C)(C)C IDHNOWGENVCVSX-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000004503 fine granule Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229940099552 hyaluronan Drugs 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 210000000260 male genitalia Anatomy 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YMKSUNUZQDIVIE-UHFFFAOYSA-N methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C=1N=C(Br)SC=1C YMKSUNUZQDIVIE-UHFFFAOYSA-N 0.000 description 1
- SSXZSQHXBWITRI-UHFFFAOYSA-N methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=N1 SSXZSQHXBWITRI-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N methylsulphonylmethane Natural products CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 108091040857 miR-604 stem-loop Proteins 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001483 mobilizing effect Effects 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- AUODXGUVFIPLCV-UHFFFAOYSA-N n-(2-cyclohexylethyl)-6-[[[(3-methylsulfanylphenyl)-(1-methyltetrazol-5-yl)methylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CSC1=CC=CC(C(=NOCC=2N=C(NCCC3CCCCC3)C=CC=2)C=2N(N=NN=2)C)=C1 AUODXGUVFIPLCV-UHFFFAOYSA-N 0.000 description 1
- OZYPPHLDZUUCCI-UHFFFAOYSA-N n-(6-bromopyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(Br)=N1 OZYPPHLDZUUCCI-UHFFFAOYSA-N 0.000 description 1
- ZKDMTGFOPIELEE-UHFFFAOYSA-N n-(6-bromopyridin-2-yl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC(Br)=N1 ZKDMTGFOPIELEE-UHFFFAOYSA-N 0.000 description 1
- YPWKLBCTOUEZKE-UHFFFAOYSA-N n-(6-chloropyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(Cl)=N1 YPWKLBCTOUEZKE-UHFFFAOYSA-N 0.000 description 1
- DRJJATMNDDRQOM-UHFFFAOYSA-N n-(6-formylpyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(C=O)=N1 DRJJATMNDDRQOM-UHFFFAOYSA-N 0.000 description 1
- SSXGDEUEONGPAF-UHFFFAOYSA-N n-(6-formylpyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=N1 SSXGDEUEONGPAF-UHFFFAOYSA-N 0.000 description 1
- IDMATJHPQWRTTA-UHFFFAOYSA-N n-[(3-fluoro-6-hex-1-ynylpyridin-2-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CCCCC#CC1=CC=C(F)C(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 IDMATJHPQWRTTA-UHFFFAOYSA-N 0.000 description 1
- HJYLLBKMHUCJJG-UHFFFAOYSA-N n-[(5-methyl-2-pent-1-ynyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound S1C(C#CCCC)=NC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=C1C HJYLLBKMHUCJJG-UHFFFAOYSA-N 0.000 description 1
- HFJLUKXQIRWPLD-UHFFFAOYSA-N n-[(6-hex-1-ynylpyridin-2-yl)methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CCCCC#CC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 HFJLUKXQIRWPLD-UHFFFAOYSA-N 0.000 description 1
- HVVPXHKALPZCCU-UHFFFAOYSA-N n-[[2-(2-cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CSC(C#CC2CC2)=N1 HVVPXHKALPZCCU-UHFFFAOYSA-N 0.000 description 1
- JYEYSPJHPSTBEG-AGFDQOOSSA-N n-[[2-[(e)-hex-1-enyl]-1,3-thiazol-4-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound S1C(/C=C/CCCC)=NC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=C1 JYEYSPJHPSTBEG-AGFDQOOSSA-N 0.000 description 1
- USPWWVACYDNDJD-UHFFFAOYSA-N n-[[5-chloro-2-(2-cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=C(Cl)SC(C#CC2CC2)=N1 USPWWVACYDNDJD-UHFFFAOYSA-N 0.000 description 1
- XVCQIFMEBNBAJE-UHFFFAOYSA-N n-[[6-(2-cyclopropylethynyl)-5-methoxypyridin-2-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound N1=C(C#CC2CC2)C(OC)=CC=C1CON=C(C=1C=CC=CC=1)C1=NN=NN1C XVCQIFMEBNBAJE-UHFFFAOYSA-N 0.000 description 1
- NTLAJUPNHPRTHP-DMSJEEJQSA-N n-[[6-[(e)-2-cyclohexylethenyl]pyridin-2-yl]methoxy]-1-(1-methyltetrazol-5-yl)-1-phenylmethanimine Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(\C=C\C2CCCCC2)=N1 NTLAJUPNHPRTHP-DMSJEEJQSA-N 0.000 description 1
- UZUZAJPCSOZMGF-UHFFFAOYSA-N n-[[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]methyl]hexanamide Chemical compound CCCCCC(=O)NCC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 UZUZAJPCSOZMGF-UHFFFAOYSA-N 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 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
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229950006238 nadide Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- JOUIQRNQJGXQDC-ZYUZMQFOSA-L nicotinate D-ribonucleotide(2-) Chemical compound O1[C@H](COP([O-])([O-])=O)[C@@H](O)[C@@H](O)[C@@H]1[N+]1=CC=CC(C([O-])=O)=C1 JOUIQRNQJGXQDC-ZYUZMQFOSA-L 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 101150038594 nodC gene Proteins 0.000 description 1
- GHLZUHZBBNDWHW-UHFFFAOYSA-N nonanamide Chemical compound CCCCCCCCC(N)=O GHLZUHZBBNDWHW-UHFFFAOYSA-N 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000004536 oil dispersible powder Substances 0.000 description 1
- 239000004535 oil miscible liquid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008723 osmotic stress Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000157 polyfructose Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- PAQVEXAFKDWGOT-UHFFFAOYSA-N prop-2-ynoxymethylbenzene Chemical compound C#CCOCC1=CC=CC=C1 PAQVEXAFKDWGOT-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- CJBORKPPXVPALH-UHFFFAOYSA-N s-butyl n-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]carbamothioate Chemical compound CCCCSC(=O)NC1=CC=CC(CON=C(C=2N(N=NN=2)C)C=2C=CC=CC=2)=N1 CJBORKPPXVPALH-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 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
- 150000004760 silicates Chemical class 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- VYFPSYVVFFFYBF-UHFFFAOYSA-N sodium;triphenylphosphane Chemical compound [Na].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VYFPSYVVFFFYBF-UHFFFAOYSA-N 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- URHWNXDZOULUHC-UHFFFAOYSA-N tert-butyl n-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]carbamate Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(NC(=O)OC(C)(C)C)=N1 URHWNXDZOULUHC-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005936 thiocarbonylation reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004564 water dispersible powder for slurry treatment Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000004553 water soluble powder for seed treatment Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000002916 wood waste Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (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)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08356047 | 2008-03-19 | ||
| EP08356047.4 | 2008-03-19 | ||
| PCT/EP2009/053208 WO2009115557A2 (en) | 2008-03-19 | 2009-03-18 | Fungicide hydroximoyl-tetrazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520778A JP2011520778A (ja) | 2011-07-21 |
| JP2011520778A5 JP2011520778A5 (enExample) | 2011-09-15 |
| JP5571062B2 true JP5571062B2 (ja) | 2014-08-13 |
Family
ID=39673452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500217A Expired - Fee Related JP5571062B2 (ja) | 2008-03-19 | 2009-03-18 | 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8466176B2 (enExample) |
| EP (1) | EP2265118A2 (enExample) |
| JP (1) | JP5571062B2 (enExample) |
| KR (1) | KR20100125424A (enExample) |
| CN (1) | CN101977504B (enExample) |
| BR (1) | BRPI0906023A2 (enExample) |
| CO (1) | CO6280584A2 (enExample) |
| MX (1) | MX2010010135A (enExample) |
| WO (1) | WO2009115557A2 (enExample) |
| ZA (1) | ZA201006312B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2527024C2 (ru) * | 2008-01-15 | 2014-08-27 | Байер Кропсайенс Аг | Пестицидная композиция, содержащая производное тетразолилоксима и активное фунгицидное или инсектицидное вещество (варианты) и способ борьбы с фитопатагенными грибами или вредоносными насекомыми |
| KR20100125426A (ko) * | 2008-03-19 | 2010-11-30 | 바이엘 크롭사이언스 아게 | 살진균제 히드록시모일-테트라졸 유도체 |
| EP2257168B1 (en) * | 2008-03-19 | 2013-06-05 | Bayer Intellectual Property GmbH | Fungicide hydroximoyl-tetrazole derivatives |
| CA2728469A1 (en) * | 2008-07-04 | 2010-01-07 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
| CA2728474A1 (en) * | 2008-07-04 | 2010-01-07 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
| JP5550913B2 (ja) * | 2009-01-05 | 2014-07-16 | 日本曹達株式会社 | テトラゾイルオキシム誘導体およびその塩、並びに植物病害防除剤 |
| JP5542452B2 (ja) * | 2009-01-05 | 2014-07-09 | 日本曹達株式会社 | テトラゾイルオキシム誘導体およびその塩、ならびに植物病害防除剤 |
| JP5782658B2 (ja) * | 2009-12-28 | 2015-09-24 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺菌剤ヒドロキシモイル−テトラゾール誘導体 |
| EP2719688B1 (en) * | 2010-03-12 | 2016-07-20 | Nippon Soda Co., Ltd. | Process for producing tetrazolyloxime derivatives |
| AU2014201036B2 (en) * | 2010-04-06 | 2015-07-16 | Nippon Soda Co., Ltd | Nitrogen-containing heterocyclic compound and method for producing same |
| US8703959B2 (en) | 2010-04-06 | 2014-04-22 | Nippon Soda Co., Ltd | Nitrogen-containing heterocyclic compound and method for producing same |
| WO2011134911A2 (en) * | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
| BR112013008446B1 (pt) | 2010-10-07 | 2018-06-12 | Bayer Cropscience Ag | ''composição e método para controlar os fungos fitopatogênicos ou insetos danificadores de plantas,safras ou sementes'' |
| WO2012117021A2 (en) * | 2011-03-03 | 2012-09-07 | Syngenta Participations Ag | Novel microbiocidal oxime ethers |
| EP2826773B1 (en) * | 2012-03-13 | 2016-11-02 | Nippon Soda Co., Ltd. | Compound, method for producing compound, and method for purifying compound |
| ES2739323T3 (es) * | 2013-03-05 | 2020-01-30 | Nippon Soda Co | Método de control de hongos del género Rhizopus en arroz |
| EP3330253B1 (en) * | 2015-07-28 | 2019-09-25 | Nippon Soda Co., Ltd. | Pyridine-2-yl-pyridinium compound and method of using same |
| WO2018069108A1 (en) | 2016-10-10 | 2018-04-19 | Basf Se | Pesticidal mixtures |
| WO2018069110A1 (en) | 2016-10-10 | 2018-04-19 | Basf Se | Pesticidal mixtures |
| BR122022025239B1 (pt) | 2016-10-10 | 2023-10-31 | Basf Se | Mistura pesticida, composição pesticida, métodos para controlar pragas fitopatogênicas, para melhorar a saúde de plantas e para a proteção do material de propagação vegetal contra pragas e material de propagação vegetal |
| BR112021015521A2 (pt) | 2019-02-20 | 2021-10-05 | Basf Se | Misturas de pesticidas, método para controlar fungos nocivos fitopatogênicos e método para proteger plantas em crescimento ou materiais de propagação de plantas do ataque ou infestação por pragas invertebradas |
| CN112110911B (zh) * | 2019-06-19 | 2024-04-26 | 东莞市东阳光农药研发有限公司 | 1,3,4-噁二唑类肟衍生物及其制备方法和应用 |
| KR102345734B1 (ko) | 2019-06-21 | 2021-12-31 | 주식회사 라파스 | 최소 침습적 바이오 센싱을 위한 생체적합성이고 전기전도성인 고분자 마이크로니들 바이오 센서 |
| CN112979628B (zh) * | 2019-12-12 | 2024-04-26 | 东莞市东阳光农药研发有限公司 | 二苯醚取代的肟类衍生物及其在农业中的应用 |
| CN112979633B (zh) * | 2019-12-12 | 2024-02-02 | 东莞市东阳光农药研发有限公司 | 新的肟类衍生物及其制备方法和应用 |
| CN114685392A (zh) * | 2020-12-28 | 2022-07-01 | 东莞市东阳光农药研发有限公司 | 一种苯基-四唑肟类衍生物及其制备方法和应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2581063B1 (fr) * | 1985-04-30 | 1987-07-17 | Chauvin Blache Lab | Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique |
| US4933355A (en) * | 1988-04-14 | 1990-06-12 | Sankyo Company Limited | Thiazole derivatives, their preparation and their use in the treatment of diabetes complications |
| FR2687149B1 (fr) * | 1992-02-12 | 1995-11-03 | Roussel Uclaf | Nouveaux esters pyrethrinouides derives d'alcools thiazoliques, leur procede de preparation et leur application comme pesticides. |
| US5455351A (en) * | 1993-12-13 | 1995-10-03 | Abbott Laboratories | Retroviral protease inhibiting piperazine compounds |
| RO121119B1 (ro) * | 1997-12-10 | 2006-12-29 | Dainippon Ink And Chemicals, Inc. | Derivaţi de oximă şi chimicale pentru agricultură, incluzând aceşti derivaţi |
| US6472386B1 (en) * | 2001-06-29 | 2002-10-29 | Kowa Co., Ltd. | Cyclic diamine compound with 5-membered ring groups |
| AR035087A1 (es) * | 2001-08-09 | 2004-04-14 | Syngenta Participations Ag | Piridil-alquinos y piridil-n-oxido-alquinos herbicidas activos, procedimiento para su preparacion, composicion herbicida y para inhibir el crecimiento de plantas, metodo para el control del crecimiento de plantas indeseables , y metodo para la inhibicion del crecimiento de plantas |
| JP4330313B2 (ja) * | 2001-08-20 | 2009-09-16 | 日本曹達株式会社 | テトラゾイルオキシム誘導体及びこれを有効成分とする農薬 |
| WO2003016303A1 (en) * | 2001-08-20 | 2003-02-27 | Dainippon Ink And Chemicals, Inc. | Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient |
| AR037754A1 (es) * | 2001-12-11 | 2004-12-01 | Syngenta Participations Ag | Herbicidas |
| JP2004131392A (ja) * | 2002-10-08 | 2004-04-30 | Sumitomo Chem Co Ltd | テトラゾール化合物およびその用途 |
| JP2004131416A (ja) * | 2002-10-10 | 2004-04-30 | Sumitomo Chem Co Ltd | テトラゾール化合物およびその植物病害防除用途 |
| JP2007502298A (ja) * | 2003-08-14 | 2007-02-08 | スミスクライン ビーチャム コーポレーション | 化合物 |
| DE102004016845A1 (de) | 2004-04-07 | 2005-10-27 | Bayer Healthcare Ag | Phenylthioessigsäure-Derivate und ihre Verwendung |
| TWI346109B (en) * | 2004-04-30 | 2011-08-01 | Otsuka Pharma Co Ltd | 4-amino-5-cyanopyrimidine derivatives |
| WO2008006873A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
| AU2007274274B2 (en) * | 2006-07-13 | 2012-10-04 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
| CA2653698A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
| US8084613B2 (en) * | 2007-05-14 | 2011-12-27 | Nippon Soda Co., Ltd. | Tetrazoyloxime derivative and plant disease control agent |
| EP2177519B1 (en) | 2007-08-08 | 2015-05-27 | Nippon Soda Co., Ltd. | Tetrazoyloxime derivative and plant disease control agent |
| US20100286173A1 (en) * | 2008-01-16 | 2010-11-11 | Christian Beier | Fungicide hydroximoyl-tetrazole derivatives |
-
2009
- 2009-03-18 KR KR1020107023225A patent/KR20100125424A/ko not_active Withdrawn
- 2009-03-18 JP JP2011500217A patent/JP5571062B2/ja not_active Expired - Fee Related
- 2009-03-18 EP EP09721227A patent/EP2265118A2/en not_active Withdrawn
- 2009-03-18 WO PCT/EP2009/053208 patent/WO2009115557A2/en not_active Ceased
- 2009-03-18 CN CN200980109889.4A patent/CN101977504B/zh not_active Expired - Fee Related
- 2009-03-18 BR BRPI0906023-5A patent/BRPI0906023A2/pt not_active IP Right Cessation
- 2009-03-18 US US12/933,276 patent/US8466176B2/en not_active Expired - Fee Related
- 2009-03-18 MX MX2010010135A patent/MX2010010135A/es active IP Right Grant
-
2010
- 2010-09-02 ZA ZA2010/06312A patent/ZA201006312B/en unknown
- 2010-09-15 CO CO10114368A patent/CO6280584A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009115557A2 (en) | 2009-09-24 |
| EP2265118A2 (en) | 2010-12-29 |
| KR20100125424A (ko) | 2010-11-30 |
| JP2011520778A (ja) | 2011-07-21 |
| ZA201006312B (en) | 2013-02-27 |
| US8466176B2 (en) | 2013-06-18 |
| MX2010010135A (es) | 2010-10-25 |
| CN101977504B (zh) | 2014-11-26 |
| CN101977504A (zh) | 2011-02-16 |
| CO6280584A2 (es) | 2011-05-20 |
| BRPI0906023A2 (pt) | 2015-06-30 |
| WO2009115557A3 (en) | 2009-11-26 |
| US20110105566A1 (en) | 2011-05-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5571062B2 (ja) | 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 | |
| JP5615803B2 (ja) | 殺真菌剤ヒドロキシモイル−ヘテロ環誘導体 | |
| US20110201613A1 (en) | Fungicide hydroximoyl-tetrazole derivatives | |
| CN101970423A (zh) | 杀真菌剂肟基-四唑衍生物 | |
| EP2257168B1 (en) | Fungicide hydroximoyl-tetrazole derivatives | |
| EP2303865B1 (en) | Fungicide hydroximoyl-tetrazole derivatives | |
| JP2016511263A (ja) | 殺菌性３−｛ヘテロシクリル［（ヘテロシクリルメトキシ）イミノ］メチル｝−オキサジアゾロン誘導体 | |
| US9743665B2 (en) | Fungicidal 3-{phenyl[heterocyclylmethoxy)imino]methyl}-oxadiazolone derivatives | |
| CN102216286A (zh) | 作为植物保护剂的取代的(吡啶基)-嗪基胺衍生物 | |
| HK1156035A (en) | Fungicide hydroximoyl-heterocycles derivatives | |
| JP2016515100A (ja) | 殺菌性３−｛フェニル［（ヘテロシクリルメトキシ）イミノ］メチル｝−ヘテロ環誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20110721 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110722 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20111115 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131003 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131008 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140106 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140114 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140407 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140527 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140625 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5571062 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |