JP2022509696A - 殺微生物性2-アシルアミノ-チアゾール-4-カルボキサミド誘導体 - Google Patents
殺微生物性2-アシルアミノ-チアゾール-4-カルボキサミド誘導体 Download PDFInfo
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- JP2022509696A JP2022509696A JP2021531278A JP2021531278A JP2022509696A JP 2022509696 A JP2022509696 A JP 2022509696A JP 2021531278 A JP2021531278 A JP 2021531278A JP 2021531278 A JP2021531278 A JP 2021531278A JP 2022509696 A JP2022509696 A JP 2022509696A
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- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 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
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- LVRDWSMHAOIPMQ-UHFFFAOYSA-N tetradeca-10,12-dienoic acid Chemical compound CC=CC=CCCCCCCCCC(O)=O LVRDWSMHAOIPMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000005326 tetrahydropyrimidines Chemical class 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- XHCWDWXHTFMHAT-UHFFFAOYSA-J tetrasodium methanethioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C=S.[O-]C=S.[O-]C=S.[O-]C=S XHCWDWXHTFMHAT-UHFFFAOYSA-J 0.000 description 1
- OUOJIFQQBPKAMU-UHFFFAOYSA-N tetrazol-5-one Chemical compound O=C1N=NN=N1 OUOJIFQQBPKAMU-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
- 229960004906 thiomersal Drugs 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 description 1
- 229960004885 tiamulin Drugs 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- MLFGIRNMAOXTHS-UHFFFAOYSA-N tris(2-methylaziridin-1-yl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC1CN1P(=S)(N1C(C1)C)N1C(C)C1 MLFGIRNMAOXTHS-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
- 229950006929 uredepa Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- FVECELJHCSPHKY-YFUMOZOISA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-YFUMOZOISA-N 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
YはC-F、C-H又はNであり;
R1は、水素、C1~C6アルキル、C1~C6アルコキシ、C1~C6ハロアルキル、C1~C6ヒドロキシアルキル、C1~C6アルコキシC1~C6アルキル、C3~C6シクロアルキル、C1~C6アルコキシC1~C3アルコキシ、C1~C6アルコキシカルボニル、C1~C6アルコキシカルボニルC1~C4アルキル、C1~C6アルコキシカルボニルオキシC1~C4アルキル、C1~C6アルキルカルボニルオキシC1~C4アルキル、C2~C6アルケニルオキシ、C2~C6アルキニルオキシ、C1~C6アルキルスルファニル、ジ(C1~C6アルキル)アミノ、フェニル、フェニルC1~C3アルキル、フェニルC1~C3アルコキシC1~C3アルキル、フェノキシ又はヘテロアリール(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1又は2個のヘテロ原子を含む5員又は6員芳香族単環式環である)であり;
R2は、水素、ハロゲン、シアノ、C1~C4アルキル、C1~C4アルコキシ、C1~C4ハロアルキル又はHC(O)NH-であり;
R3は、C1~C8アルキル、C1~C8ハロアルキル、C1~C8アルコキシ、C3~C8シクロアルキル、C3~C8シクロアルキルC1~C2アルキル(ここで、シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)、フェニル、フェニルC1~C2アルキル、ヘテロアリール、ヘテロアリールC1~C2アルキル(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1、2、3又は4個のヘテロ原子を含む5員又は6員芳香族単環式環である)、ヘテロシクリル、ヘテロシクリルC1~C2アルキル(ここで、ヘテロシクリルは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む4員、5員又は6員非芳香族単環式環である)、又は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジ-又はカルボトリ-シクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
R4は、ハロゲン、C1~C4アルキル、C1~C4アルコキシ又はC1~C4ハロアルキルであり;
XはN又はC-Hである)
又は、その塩若しくはN-オキシドが提供されている。
R1は、水素、C1~C6アルキル、C1~C6アルコキシ、C1~C6ハロアルキル、C1~C6ヒドロキシアルキル、C1~C6アルコキシC1~C6アルキル、C3~C6シクロアルキル、C1~C6アルコキシC1~C3アルコキシ、C1~C6アルコキシカルボニル、C1~C6アルコキシカルボニルC1~C4アルキル、C1~C6アルコキシカルボニルオキシC1~C4アルキル、C1~C6アルキルカルボニルオキシC1~C4アルキル、C2~C6アルケニルオキシ、C2~C6アルキニルオキシ、C1~C6アルキルスルファニル、ジ(C1~C6アルキル)アミノ、フェニル、フェニルC1~C3アルキル、フェニルC1~C3アルコキシC1~C3アルキル、フェノキシ又はヘテロアリール(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1又は2個のヘテロ原子を含む5員又は6員芳香族単環式環である)であり;
R2はメチルであり;
R3は、C1~C8アルキル、C1~C8ハロアルキル、C1~C8アルコキシ、C3~C8シクロアルキル、C3~C8シクロアルキルC1~C2アルキル(ここで、シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)、フェニル、フェニルC1~C2アルキル、ヘテロアリール、ヘテロアリールC1~C2アルキル(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1、2、3又は4個のヘテロ原子を含む5員又は6員芳香族単環式環である)、ヘテロシクリル、ヘテロシクリルC1~C2アルキル(ここで、ヘテロシクリルは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む4員、5員又は6員非芳香族単環式環である)、又は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジ-又はカルボトリ-シクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
R4は、ハロゲン、C1~C4アルキル、C1~C4アルコキシ又はC1~C4ハロアルキルであり;
XはCNであり;並びに
YはC-Fである。
R2はメチルであり;
R3は、C3~C8シクロアルキル(ここで、シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)であり、又は、R3は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジシクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
XはNであり;並びに
YはC-Fである。
R2はメチルであり;
R3は、シクロブチル、2,2-ジメチルシクロブチル又はスピロ[3.4]オクタン-3-イルであり;
XはNであり;並びに
YはC-Fである。
R2はメチルであり;
R3は、シクロブチル、2,2-ジメチルシクロブチル又はスピロ[3.4]オクタン-3-イルであり;
XはNであり;並びに
YはC-Fである。
R1は、水素、C1~C6アルキル、C1~C6アルコキシ、C1~C6ハロアルキル、C1~C6アルコキシC1~C6アルキル、C3~C6シクロアルキル、C1~C6アルコキシC1~C3アルコキシ、C1~C6アルコキシカルボニル、C1~C6アルコキシカルボニルC1~C4アルキル、C2~C6アルケニルオキシ、C2~C6アルキニルオキシ、C1~C6アルキルスルファニル、フェニル、フェノキシ又はヘテロアリール(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1又は2個のヘテロ原子を含む5員又は6員芳香族単環式環である)であり;
R2はメチルであり;
R3は、C1~C8アルキル、C1~C8ハロアルキル、C1~C8アルコキシ、C3~C8シクロアルキル、C3~C8シクロアルキルC1~C2アルキル(ここで、シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)、フェニル、フェニルC1~C2アルキル、ヘテロアリール、ヘテロアリールC1~C2アルキル(ここで、ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1、2、3又は4個のヘテロ原子を含む5員又は6員芳香族単環式環である)、ヘテロシクリル、ヘテロシクリルC1~C2アルキル(ここで、ヘテロシクリルは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む4員、5員又は6員非芳香族単環式環である)、又は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジ-又はカルボトリ-シクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
R4は、ハロゲン、C1~C4アルキル、C1~C4アルコキシ又はC1~C4ハロアルキルであり;
XはCNであり;並びに
YはC-Fである。
R2はメチルであり;
R3はC3~C8シクロアルキル(ここで、シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)であり、又は、R3は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジシクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
XはNであり;並びに
YはC-Fである。
R2はメチルであり;
R3は、シクロブチル、2,2-ジメチルシクロブチル又はスピロ[3.4]オクタン-3-イルであり;
XはNであり;並びに
YはC-Fである。
R2はメチルであり;
R3は、シクロブチル、2,2-ジメチルシクロブチル又はスピロ[3.4]オクタン-3-イルであり;
XはNであり;並びに
YはC-Fである。
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防除され得る、これらの病害に係る真菌及び真菌媒介物、並びに、植物病原性バクテリア及びウイルスは、例えば以下のとおりである。
アブシジアコリムビフェラ(Absidia corymbifera)、アルテルナリア属の一種(Alternaria spp)、アファノミセス属の一種(Aphanomyces spp)、アスコキタ属の一種(Ascochyta spp)、A.フラバス(A.flavus)、A.フミガーツス(A.fumigatus)、A.ニズランス(A.nidulans)、A.ニガー(A.niger)、A.テルス(A.terrus)を含むアスペルギルス属の一種(Aspergillus spp.)、A.プルランス(A.pullulans)を含むアウレオバシジウム属の一種(Aureobasidium spp.)、ブラストミセスデルマチチディス(Blastomyces dermatitidis)、ブルメリアグラミニス(Blumeria graminis)、ブレミアラクツカエ(Bremia lactucae)、B.ドチデア(B.dothidea)、B.オブツサ(B.obtusa)のボトリオスファエリア属の一種(Botryosphaeria spp.)、B.シネレア(B.cinerea)を含むボトリチス属の一種(Botrytis spp.)、C.アルビカンス(C.albicans)、C.グラブラータ(C.glabrata)、C.クルセイ(C.krusei)、C.ルシタニエ(C.lusitaniae)、C.パラプシロシス(C.parapsilosis)、C.トロピカリス(C.tropicalis)のカンジダ属の一種(Candida spp.)、セファロアスクスフラグランス(Cephaloascus fragrans)、セラトシスチス属の一種(Ceratocystis spp)、C.アラキジコラ(C.arachidicola)を含むセルコスポラ属の一種(Cercospora spp.)、セルコスポリジウムペルソナツム(Cercosporidium personatum)、クラドスポリウム属の一種(Cladosporium spp)、クラビセプスプルプレア(Claviceps purpurea)、
コクシジオイデスイミティス(Coccidioides immitis)、コクリオボルス属の一種(Cochliobolus spp)、C.ムサエ(C.musae)を含むコレトトリカム属の一種(Colletotrichum spp.)、
クリプトコッカスネオフォルマンス(Cryptococcus neoformans)、ジアポルテ属の一種(Diaporthe spp)、ジディメラ属の一種(Didymella spp)、ドレックスレラ属の一種(Drechslera spp)、エルシノエ属の一種(Elsinoe spp)、
エピデルモフィトン属の一種(Epidermophyton spp)、エルウィニアアミロボラ(Erwinia amylovora)、E.シコラセアルム(E.cichoracearum)を含むエリシフェ種(Erysiphe spp.)、
ユーチパラタ(Eutypa lata)、F.クルモルム(F.culmorum)、F.グラミネアルム(F.graminearum)、F.ラングセチエ(F.langsethiae)、F.モニリホルメ(F.moniliforme)、F.オキシスポルム(F.oxysporum)、F.プロリフェラツム(F.proliferatum)、F.スブグルチナンス(F.subglutinans)、F.ソラニ(F.solani)を含むフザリウム属の一種(Fusarium spp.)、ゲーウマノミセスグラミニス(Gaeumannomyces graminis)、ギベレラフジクロイ(Gibberella fujikuroi)、グロエオデスポミゲナ(Gloeodes pomigena)、グロエオスポリウムムサルム(Gloeosporium musarum)、グロメレラシングレート(Glomerella cingulate)、ガイグナルディアビドウェリイ(Guignardia bidwellii)、ギムノスポランギウム ジュニペリ-ヴィルギニアネ(Gymnosporangium juniperi-virginianae)、ヘルミントスポリウム属の一種(Helminthosporium spp)、ヘミレイア属の一種(Hemileia spp)、H.カプスラツム(H.capsulatum)を含むヒストプラズマ属の一種(Histoplasma spp.)、ラエチサリアフシホルミス(Laetisaria fuciformis)、レプトグラフィウムリンドベルギ(Leptographium lindbergi)、レベイルラタウリカ(Leveillula taurica)、ロフォデルミウムセディチオスム(Lophodermium seditiosum)、コムギ赤かび病菌(Microdochium nivale)、ミクロスポルム属の一種(Microsporum spp)、モニリニア属の一種(Monilinia spp)、ムコール属の一種(Mucor spp)、コムギ葉枯病菌(M.graminicola)、M.ポミ(M.pomi)を含むミコスファエレラ属の一種(Mycosphaerella spp.)、オンコバシジウムテオブロマエオン(Oncobasidium theobromaeon)、オフィオストマピセエ(Ophiostoma piceae)、パラコジディオイデス属の一種(Paracoccidioides spp)、P.ディジタツム(P.digitatum)、P.イタリクム(P.italicum)を含むペニシリウム属の一種(Penicillium spp.)、ペトリエリジウム属の一種(Petriellidium spp)、P.メイディス(P.maydis)、P.フィリピネンシス(P.philippinensis)及びP.ソルギ(P.sorghi)を含むペロノスクレロスポラ属の一種(Peronosclerospora spp.)、ペロノスポラ属の一種(Peronospora spp)、コムギふ枯病菌(Phaeosphaeria nodorum)、ファコプソラパチリジ(Phakopsora pachyrhizi)、フェリヌスイグニアルス(Phellinus igniarus)、フィアロフォラ属の一種(Phialophora spp)、フォーマ属の一種(Phoma spp)、ホモプシスビティコーラ(Phomopsis viticola)、P.インフェスタンス(P.infestans)を含むフィトフトラ属の一種(Phytophthora spp.)、P.ハルステジイ(P.halstedii)、P.ビチコラ(P.viticola)を含むプラスモパラ属の一種(Plasmopara spp.)、プレオスポラ属の一種(Pleospora spp.)、リンゴうどんこ病菌(P.leucotricha)を含むポドスファエラ属の一種(Podosphaera spp.)、ポリミキサグラミニス(Polymyxa graminis)、ポリミキサベタエ(Polymyxa betae)、シュードセルコスポレラヘルポトリコイド(Pseudocercosporella herpotrichoides)、シュードモナス属の一種(Pseudomonas spp)、P.クベンシス(P.cubensis)、P.フムリ(P.humuli)を含むシュードペロノスポラ属の一種(Pseudoperonospora spp.)、シュードペジザトラケイフィラ(Pseudopeziza tracheiphila)、P.ホルデイ(P.hordei)、P.レコンディタ(P.recondita)、P.ストリイホルミス(P.striiformis)、P.トリチシナ(P.triticina)を含むプッシニア属の一種(Puccinia spp.)、ピレノペジザ属の一種(Pyrenopeziza spp)、ピレノホラ属の一種(Pyrenophora spp)、イネいもち病菌(P.oryzae)を含むピリクラリア属の一種(Pyricularia spp.)、P.ウルチムム(P.ultimum)を含むピシウム属の一種(Pythium spp.)、ラムラリア属の一種(Ramularia spp)、リゾクトニア属の一種(Rhizoctonia spp)、リゾムコールプシルス(Rhizomucor pusillus)、リゾプスアリズス(Rhizopus arrhizus)、リンコスポリウム属の一種(Rhynchosporium spp)、S.アピオスペルムム(S.apiospermum)及びS.プロリフィカンス(S.prolificans)を含むセドスポリウム属の一種(Scedosporium spp.)、スキゾチリウムポミ(Schizothyrium pomi)、
スクレロチニア属の一種(Sclerotinia spp)、スクレロチウム属の一種(Sclerotium spp)、S.ノドルム(S.nodorum)、S.トリティシ(S.tritici)を含むセプトリア属の一種(Septoria spp)、スファエロテカマクラリス(Sphaerotheca macularis)、スファエロテカフスカ(Sphaerotheca fusca)(スファエロテカフリギネア(Sphaerotheca fuliginea))、スポロトリクス属の一種(Sporothorix spp)、スタゴノスポラノドルム(Stagonospora nodorum)、ステムフィリウム属の一種(Stemphylium spp.)、ステレウムヒルスツム(Stereum hirsutum)、タナテホルスククメリス(Thanatephorus cucumeris)、チエラビオプシスバシコラ(Thielaviopsis basicola)、チレチア属の一種(Tilletia spp)、T.ハルジアヌム(T.harzianum)、T.シュードコニンギイ(T.pseudokoningii)、T.ヴィリデ(T.viride)を含むトリコデルマ属の一種(Trichoderma spp.)、
トリコフィトン属の一種(Trichophyton spp)、チフラ属の一種(Typhula spp)、ウンシヌラネカトル(Uncinula necator)、ウロシスチス(Urocystis spp)、ウスチラゴ属の一種(Ustilago spp)、V.イナエクアリス(V.inaequalis)を含むベンチュリア属の一種(Venturia spp.)、ベルチシリウム属の一種(Verticillium spp)及びキサントモナス属の一種(Xanthomonas spp)。
1.Syngenta Seeds SAS,Chemin de l’Hobit 27,F-31 790 St.Sauveur,France製Bt11トウモロコシ、登録番号C/FR/96/05/10。切断型Cry1Abトキシンのトランスジェニック発現により、アワノメイガ(ヨーロッパアワノメイガ(Ostrinia nubilalis)及びセサミアノナグリオイデス(Sesamia nonagrioides))に対する耐性が付与された遺伝子操作されたトウモロコシ(Zea mays)。Bt11トウモロコシはまた、酵素PATをトランスジェニック発現して除草剤グルホシネートアンモニウムに対する耐性を達成している。
-イニル)アミノ-3,5-キシリルメチルカルバメート、5,5-ジメチル-3-オキソシクロヘキサ-1-エニルジメチルカルバメート、アセチオン、アクリロニトリル、アルドリン、アロサミジン、アリキシカルブ、α-エクジソン、リン化アルミニウム、アミノカルブ、アナバシン、アチダチオン、アザメチホス、バチルスチューリンゲンシス(Bacillus thuringiensis)δエンドトキシン、バリウムヘキサフルオロシリケート、バリウムポリスルフィド、バルトリン、バイエル22/190、バイエル22408、β-シフルトリン、β-シペルメトリン、バイオエタノメトリン、ビオパーメトリン、ビス(2-クロロエチル)エーテル、ホウ酸ナトリウム、ブロムフェンビンホス、ブロモ-DDT、ブフェンカルブ、ブタカルブ、ブタチオホス、ブトネート、ヒ酸カルシウム、シアン化カルシウム、二硫化炭素、四塩化炭素、カルタップヒドロクロリド、セバジン、クロルビシクレン、クロルダン、クロルデコン、クロロホルム、クロルピクリン、クロルホキシム、クロルプラゾホス、シス-レスメスリン、シスメトリン、クロシトリン、アセト亜ヒ酸銅、ヒ酸銅、オレイン酸銅、クミトエート、氷晶石、CS708、シアノフェンホス、シアノホス、シクレトリン、シチオエート、d-テトラメトリン、DAEP、ダゾメット、デカルボフラン、ジアミダホス、ジカプトン、ジクロロフェンチオン、ジクレシル、ジシクラニル、ディルドリン、ジエチル5-メチルピラゾール-3-イルリン酸塩、ジロール、ジメフルトリン、ジメタン、ジメトリン、ジメチルビンホス、ジメチラン、ジノプロプ、ジノサム、ジノセブ、ジオフェノラン、ジオキサベンゾホス、ジチクロホス、DSP、エクジステロン、EI 1642、EMPC、EPBP、エタホス、エチオフェンカルブ、ギ酸エチル、エチレンジブロミド、ジクロロエタン、エチレンオキシド、EXD、フェンクロルホス、フェネタカルブ、フェニトロチオン、フェノキサクリム、フェンピリトリン、フェンスルホチオン、フェンチオン-エチル、フルコフロン、ホスメチラン、ホスピレート、ホスチエタン、フラチオカルブ、フレトリン、グアザチン、グアザチン酢酸塩、テトラチオカルボン酸ナトリウム、ハルフェンプロクス、HCH、HEOD、ヘプタクロール、ヘテロホス、HHDN、シアン化水素、ヒキンカルブ、IPSP、イサゾホス、イソベンザン、イソドリン、イソフェンホス、イソラン、イソプロチオラン、イソキサチオン、幼虫ホルモンI、幼虫ホルモンII、幼虫ホルモンIII、ケレバン、キノプレン、砒酸鉛、レプトホス、リリムホス、リチダチオン、m-クメニルメチルカルバメート、リン化マグネシウム、マジドクス、メカルホン、メナゾン、塩化第一水銀、メスルフェンホス、メタム、メタム-カリウム、メタム-ナトリウム、メタンフッ化スルホニル、メトクロトホス、メトプレン、メトトリン、メトキシクロル、メチルイソチオシアネート、メチルクロロホルム、塩化メチレン、メトキサジアゾン、ミレックス、ナフタロホス、ナフタレン、NC-170、ニコチン、ニコチンスルフェート、ニチアジン、ノルニコチン、O-5-ジクロロ-4-ヨードフェニルO-エチルエチルホスホノチオエート、O,O-ジエチルO-4-メチル-2-オキソ-2H-クロメン-7-イルホスホロチオネート、O,O-ジエチルO-6-メチル-2-プロピルピリミジン-4-イルホスホロチオネート、O,O,O’,O’-テトラプロピルジチオピロホスフェート、オレイン酸、パラ-ジクロロベンゼン、パラチオン-メチル、ペンタクロロフェノール、ラウリン酸ペンタクロロフェニル、PH60-38、フェンカプトン、ホスニクロル、ホスフィン、ホキシム-メチル、ピリメタホス、ポリクロロジシクロペンタジエン異性体、亜ヒ酸カリウム、カリウムチオシアネート、プレコセンI、プレコセンII、プレコセンIII、ピリミドホス、プロフルトリン、プロメカルブ、プロチオホス、ピラゾホス、ピレスメトリン、カッシア、キナルホス-メチル、キノチオン、ラホキサニド、レスメスリン、ロテノン、カデトリン、リアニア、リアノジン、サバジラ)、シュラダン、セブホス、SI-0009、チアプロニル、亜ヒ酸ナトリウム、シアン化ナトリウム、ナトリウムフッ化物、ヘキサフルオロケイ酸ナトリウム、ペンタクロロフェノキシドナトリウム塩、セレン酸ナトリウム、チオシアン酸ナトリウム、スルコフロン、スルコフロン-ナトリウム、スルフリルフッ化物、スルプロホス、タール油、チオナジン、TDE、テブピリムホス、テメホス、テラレスリン、テトラクロロエタン、チクロホス、チオシクラム、チオシクラム水素オキサレート、チオナジン、チオスルタップ、チオスルタップ-ナトリウム、トラロメトリン、トランスパーメトリン、トリアザメート、トリクロルメタホス-3、トリクロロナト、トリメタカルブ、トルプロカルブ、トリクロピリカルブ、トリプレン、ベラトリジン、ベラトリン、XMC、ζメトリン、亜鉛ホスフィド、ゾラプロホス、及びメペルフルトリン、テトラメチルフルトリン、ビス(トリブチルスズ)オキシド、ブロモアセタミド、第二鉄リン酸塩、ニクロスアミド-オラミン、酸化トリブチルスズ、ピリモルフ、トリフェンモルフ、1,2-ジブロモ-3-クロロプロパン、1,3-ジクロロプロペン、3,4-ジクロロテトラヒドロチオフェン1,1-ジオキシド、3-(4-クロロフェニル)-5-メチルロダニン、5-メチル-6-チオキソ-1,3,5-チアジアジナン-3-イル酢酸、6-イソペンテニルアミノプリン、ベンクロチアズ、サイトカイニン、DCIP、ルフラール、イサミドホス、カイネチン、ミロテシウムベルカリア(Myrothecium verrucaria)組成物、テトラクロロチオフェン、キシレノルス、ゼアチン、エチルキサントゲン酸カリウム、アシベンゾラル、アシベンゾラル-S-メチル、オオイタドリ(Reynoutria sachalinensis)抽出物、α-クロロヒドリン、アンツ、炭酸バリウム、ビスチオセミ、ブロジファクム、ブロマジオロン、ブロメタリン、クロロファシノン、コレカルシフェロール、クマクロル、クマフリル、クマテトラリル、クリミジン、ジフェナクム、ジフェチアロン、ジファシノン、エルゴカルシフェロール、フロクマフェン、フルオロアセタミド、フルプロパジン、フルプロパジンヒドロクロリド、ノルボルミド、ホスアセチム、リン、ピンドン、ピリヌロン、シリロシド、フルオロ酢酸ナトリウム、硫酸タリウム、ワルファリン、2-(2-ブトキシエトキシ)エチルピペロニレート、5-(1,3-ベンゾジオキソール-5-イル)-3-ヘキシルシクロヘキサ-2-エノン、ファルネソール+ネロリドール、ベルブチン、MGK 264、ピペロニルブトキシド、ピプロタール、プロピル異性体、S421、セサメックス、セサスモリン、スルホキシド、アントラキノン、ナフテン酸銅、オキシ塩化銅、ジシクロペンタジエン、チラム、ナフテン酸亜鉛、ジラム、イマニン、リバビリン、酸化水銀(II)、チオファネート-メチル、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジフェノコナゾール、ジニコナゾール、エポキシコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホール、フラメトピル、ヘキサコナゾール、イマザリル、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、パクロブトラゾール、ペフラゾエート、ペンコナゾール、プロチオコナゾール、ピリフェノックス、プロクロラズ、プロピコナゾール、ピリソキサゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリフルミゾール、トリチコナゾール、アンシミドール、フェナリモル、ヌアリモル、ブピリメート、ジメチリモール、エチリモール、ドデモルフ、フェンプロピジン、フェンプロピモルフ、スピロキサミン、トリデモルフ、シプロジニル、メパニピリム、ピリメタニル、フェンピクロニル、フルジオキソニル、ベナラキシル、フララキシル、メタラキシル、R-メタラキシル、オフレース、オキサジキシル、カルベンダジム、デバカルブ、フベリダゾール、チアベンダゾール、クロゾリネート、ジクロゾリン、ミクロゾリン、プロシミドン、ビンクロゾリン、ボスカリド、カルボキシン、フェンフラム、フルトラニル、メプロニル、オキシカルボキシン、ペンチオピラド、チフルザミド、ドジン、イミノクタジン、アゾキシストロビン、ジモキシストロビン、エネストロブリン、フェナミンストロビン、フルフェノキシストロビン、フルオキサストロビン、クレソキシム-メチル、メトミノストロビン、トリフロキシストロビン、オリザストロビン、ピコキシストロビン、ピラクロストロビン、ピラメトストロビン、ピラオキシストロビン、フェルバム、マンコゼブ、マンネブ、メチラム、プロピネブ、ジネブ、カプタホール、キャプタン、フルオロイミド、ホルペット、トリルフルアニド、ボルドー液、酸化銅、マンカッパー、オキシン銅、ニトロタル-イソプロピル、エディフェンホス、イプロベンホス、ホスジフェン、トルコホス-メチル、アニラジン、ベンチアバリカルブ、ブラストサイジン-S、クロロネブ、クロロタロニル、シフルフェナミド、シモキサニル、ジクロシメット、ジクロメジン、
ジクロラン、ジエトフェンカルブ、ジメトモルフ、フルモルフ、ジチアノン、エタボキサム、エトリジアゾール、ファモキサドン、フェンアミドン、フェノキサニル、フェリムゾン、フルアジナム、フルオピコリド、フルスルファミド、フルキサピロキサド、フェンヘキサミド、ホセチル-アルミニウム、ヒメキサゾール、イプロバリカルブ、シアゾファミド、メタスルホカルブ、メトラフェノン、ペンシクロン、フタリド、ポリオキシン、プロパモカルブ、ピリベンカルブ、プロキナジド、ピロキロン、ピリオフェノン、キノキシフェン、キントゼン、チアジニル、トリアゾキシド、トリシクラゾール、トリホリン、バリダマイシン、バリフェナレート、ゾキサミド、マンジプロパミド、イソピラザム、セダキサン、ベンゾビンジフルピル、ピジフルメトフェン、3-ジフルオロメチル-1-メチル-1H-ピラゾール-4-カルボン酸(3’,4’,5’-トリフルオロ-ビフェニル-2-イル)-アミド、イソフルシプラム、イソチアニル、ジピメチトロン、6-エチル-5,7-ジオキソ-ピロロ[4,5][1,4]ジチイノ[1,2-c]イソチアゾール-3-カルボニトリル、2-(ジフルオロメチル)-N-[3-エチル-1,1-ジメチル-インダン-4-イル]ピリジン-3-カルボキサミド、4-(2,6-ジフルオロフェニル)-6-メチル-5-フェニル-ピリダジン-3-カルボニトリル、(R)-3-(ジフルオロメチル)-1-メチル-N-[1,1,3-トリメチルインダン-4-イル]ピラゾール-4-カルボキサミド、4-(2-ブロモ-4-フルオロ-フェニル)-N-(2-クロロ-6-フルオロ-フェニル)-2,5-ジメチル-ピラゾール-3-アミン、4-(2-ブロモ-4-フルオロフェニル)-N-(2-クロロ-6-フルオロフェニル)-1,3-ジメチル-1H-ピラゾール-5-アミン、フルインダピル、クメトキシストロビン(ジアキシアングジュンジ(jiaxiangjunzhi))、ルベンミキシアナン(lvbenmixianan)、ジクロベンチアゾクス、マンデストロビン、3-(4,4-ジフルオロ-3,4-ジヒドロ-3,3-ジメチルイソキノリン-1-イル)キノロン、2-[2-フルオロ-6-[(8-フルオロ-2-メチル-3-キノリル)オキシ]フェニル]プロパン-2-オール、オキサチアピプロリン、t-ブチルN-[6-[[[(1-メチルテトラゾール-5-イル)-フェニル-メチレン]アミノ]オキシメチル]-2-ピリジル]カルバメート、ピラジフルミド、インピルフルキサム、ツロールプロカルブ、メフェントリフルコナゾール、イプフェントリフルコナゾール、2-(ジフルオロメチル)-N-[(3R)-3-エチル-1,1-ジメチル-インダン-4-イル]ピリジン-3-カルボキサミド、N’-(2,5-ジメチル-4-フェノキシ-フェニル)-N-エチル-N-メチル-ホルムアミジン、N’-[4-(4,5-ジクロロチアゾール-2-イル)オキシ-2,5-ジメチル-フェニル]-N-エチル-N-メチル-ホルムアミジン、[2-[3-[2-[1-[2-[3,5-ビス(ジフルオロメチル)ピラゾール-1-イル]アセチル]-4-ピペリジル]チアゾール-4-イル]-4,5-ジヒドロイソキサゾール-5-イル]-3-クロロ-フェニル]メタンスルホン酸、ブタ-3-イニルN-[6-[[(Z)-[(1-メチルテトラゾール-5-イル)-フェニル-メチレン]アミノ]オキシメチル]-2-ピリジル]カルバメート、メチルN-[[5-[4-(2,4-ジメチルフェニル)トリアゾール-2-イル]-2-メチル-フェニル]メチル]カルバメート、3-クロロ-6-メチル-5-フェニル-4-(2,4,6-トリフルオロフェニル)ピリダジン、ピリダクロメチル、3-(ジフルオロメチル)-1-メチル-N-[1,1,3-トリメチルインダン-4-イル]ピラゾール-4-カルボキサミド、1-[2-[[1-(4-クロロフェニル)ピラゾール-3-イル]オキシメチル]-3-メチル-フェニル]-4-メチル-テトラゾール-5-オン、1-メチル-4-[3-メチル-2-[[2-メチル-4-(3,4,5-トリメチルピラゾール-1-イル)フェノキシ]メチル]フェニル]テトラゾール-5-オン、アミノピリフェン、アメトクトラジン、アミスルブロム、ペンフルフェン、(Z,2E)-5-[1-(4-クロロフェニル)ピラゾール-3-イル]オキシ-2-メトキシイミノ-N,3-ジメチル-ペンタ-3-エンアミド、フロリルピコキサミド、フェンピコキサミド、テブフロキン、イププルフェノキン、キノフメリン、イソフェタミド、N-[2-[2,4-ジクロロ-フェノキシ]フェニル]-3-(ジフルオロメチル)-1-メチル-ピラゾール-4-カルボキサミド、N-[2-[2-クロロ-4-(トリフルオロメチル)フェノキシ]フェニル]-3-(ジフルオロメチル)-1-メチル-ピラゾール-4-カルボキサミド、ベンゾチオストロビン、フェナマクリル、5-アミノ-1,3,4-チアジアゾール-2-チオール亜鉛塩(2:1)、フルオピラム、フルチアニル、フルオピモミド、ピラプロポイン、ピカルブトラゾクス、2-(ジフルオロメチル)-N-(3-エチル-1,1-ジメチル-インダン-4-イル)ピリジン-3-カルボキサミド、2-(ジフルオロメチル)-N-((3R)-1,1,3-トリメチルインダン-4-イル)ピリジン-3-カルボキサミド、4-[[6-[2-(2,4-ジフルオロフェニル)-1,1-ジフルオロ-2-ヒドロキシ-3-(1,2,4-トリアゾール-1-イル)プロピル]-3-ピリジル]オキシ]ベンゾニトリル、メチルテトラプロール、2-(ジフルオロメチル)-N-((3R)-1,1,3-トリメチルインダン-4-イル)ピリジン-3-カルボキサミド、α-(1,1-ジメチルエチル)-α-[4’-(トリフルオロメトキシ)[1,1’-ビフェニル]-4-イル]-5-ピリミジンメタノール、フルオキサピプロリン、エノキサストロビン、4-[[6-[2-(2,4-ジフルオロフェニル)-1,1-ジフルオロ-2-ヒドロキシ-3-(1,2,4-トリアゾール-1-イル)プロピル]-3-ピリジル]オキシ]ベンゾニトリル、4-[[6-[2-(2,4-ジフルオロフェニル)-1,1-ジフルオロ-2-ヒドロキシ-3-(5-スルファニル-1,2,4-トリアゾール-1-イル)プロピル]-3-ピリジル]オキシ]ベンゾニトリル、4-[[6-[2-(2,4-ジフルオロフェニル)-1,1-ジフルオロ-2-ヒドロキシ-3-(5-チオキソ-4H-1,2,4-トリアゾール-1-イル)プロピル]-3-ピリジル]オキシ]ベンゾニトリル、トリネキサパック、クモキシストロビン、チョンサンマイシン(zhongshengmycin)、チオジアゾール銅、亜鉛チアゾール、アメクトトラクチン、イプロジオン、N-メトキシ-N-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]シクロプロパンカルボキサミド、N,2-ジメトキシ-N-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]プロパンアミド、N-エチル-2-メチル-N-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]プロパンアミド、1-メトキシ-3-メチル-1-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]尿素、1,3-ジメトキシ-1-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]尿素、3-エチル-1-メトキシ-1-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]尿素、N-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]プロパンアミド、4,4-ジメチル-2-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]イソキサゾリジン-3-オン、5,5-ジメチル-2-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]イソキサゾリジン-3-オン、エチル1-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]ピラゾール-4-カルボキシレート、N,N-ジメチル-1-[[4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]フェニル]メチル]-1,2,4-トリアゾール-3-アミン(これは、国際公開第2017/055473号、国際公開第2017/055469号、国際公開第2017/093348号及び国際公開第2017/118689号に記載の方法により調製され得る)、2-[6-(4-クロロフェノキシ)-2-(トリフルオロメチル)-3-ピリジル]-1-(1,2,4-トリアゾール-1-イル)プロパン-2-オール(この化合物は、国際公開第2017/029179号に記載の方法により調製され得る)、2-[6-(4-ブロモフェノキシ)-2-(トリフルオロメチル)-3-ピリジル]-1-(1,2,4-トリアゾール-1-イル)プロパン-2-オール(この化合物は、国際公開第2017/029179号に記載の方法により調製され得る)、3-[2-(1-クロロシクロプロピル)-3-(2-フルオロフェニル)-2-ヒドロキシ-プロピル]イミダゾール-4-カルボニトリル(この化合物は、国際公開第2016/156290号に記載の方法により調製され得る)、3-[2-(1-クロロシクロプロピル)-3-(3-クロロ-2-フルオロ-フェニル)-2-ヒドロキシ-プロピル]イミダゾール-4-カルボニトリル(この化合物は、国際公開第2016/156290号に記載の方法により調製され得る)、4-フェノキシフェニル)メチル2-アミノ-6-メチル-ピリジン-3-カルボキシレート(この化合物は、国際公開第2014/006945号に記載の方法により調製され得る)、2,6-ジメチル-1H,5H-[1,4]ジチイノ[2,3-c:5,6-c’]ジピロール-1,3,5,7(2H,6H)-テトロン(この化合物は、国際公開第2011/138281号に記載の方法により調製され得る)、N-メチル-4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]ベンゼンカルボチオアミド、N-メチル-4-[5-(トリフルオロメチル)-1,2,4-オキサジアゾール-3-イル]ベンズアミド、(Z,2E)-5-[1-(2,4-ジクロロフェニル)ピラゾール-3-イル]オキシ-2-メトキシイミノ-N,3-ジメチル-ペンタ-3-エンアミド(この化合物は、国際公開第2018/153707号に記載の方法により調製され得る)、N’-(2-クロロ-5-メチル-4-フェノキシ-フェニル)-N-エチル-N-メチル-ホルムアミジン、N’-[2-クロロ-4-(2-フルオロフェノキシ)-5-メチル-フェニル]-N-エチル-N-メチル-ホルムアミジン(この化合物は、国際公開第2016/202742号に記載の方法により調製され得る)、2-(ジフルオロメチル)-N-[(3S)-3-エチル-1,1-ジメチル-インダン-4-イル]ピリジン-3-カルボキサミド(この化合物は、国際公開第2014/095675号に記載の方法により調製され得る)。
有機リン酸エステル:アセフェート、アザメチホス、アジンホス-エチル、アジンホス-メチル、ブロモホス、ブロモホス-エチル、カズサホス、クロルエトキシホス、クロルピリホス、クロルフェンビンホス、クロルメホス、デメトン、デメトン-S-メチル、デメトン-S-メチルスルホン、ジアリホス、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジスルホトン、エチオン、エトプロホス、エトリムホス、ファンファー、フェナミホス、フェニトロチオン、フェンスルホチオン、フェンチオン、フルピラゾホス、フォノホス、ホルモチオン、ホスチアゼート、ヘプテノホス、イサゾホス、イソチオエート、イソキサチオン、マラチオン、メタクリホス、メタミドホス、メチダチオン、メチル-パラチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシデメトン-メチル、パラオキソン、パラチオン、パラチオン-メチル、フェントエート、ホサロン、ホスホラン、ホスホカルブ、ホスメット、ホスファミドン、ホレート、ホキシム、ピリミホス、ピリミホス-メチル、プロフェノホス、プロパホス、プロエタムホス、プロチオホス、ピラクロホス、ピリダペンチオン、キナルホス、スルプロホス、テメホス、テルブホス、テブピリムホス、テトラクロルビンホス、チメトン(thimeton)、トリアゾホス、トリクロルホン、バミドチオン。
a)R1、R2、X及びYが表1に定義されているとおりである、820種の式(I.a)の化合物。
有効成分[式(I)の化合物] 10%
オクチルフェノールポリエチレングリコールエーテル 3%
(4~5 molのエチレンオキシド)
ドデシルベンゼンスルホン酸カルシウム 3%
ヒマシ油ポリグリコールエーテル(35molのエチレンオキシド) 4%
シクロヘキサノン 30%
キシレン混合物 50%
有効成分[式(I)の化合物] 15%
リグノスルホン酸ナトリウム 2%
カルボキシメチルセルロース 1%
カオリン 82%
有効成分[式(I)の化合物] 8%
ポリエチレングリコール(mol.wt.200) 3%
カオリン 89%
有効成分[式(I)の化合物] 40%
プロピレングリコール 0%
ノニルフェノールポリエチレングリコールエーテル(15molのエチレンオキシド) 6%
リグノスルホン酸ナトリウム 10%
カルボキシメチルセルロース 1%
シリコーン油(75 %水中エマルジョンの形態) 1%
水 32%
有効成分[式(I)の化合物] 40%
プロピレングリコール 5%
コポリマーブタノールPO/EO 2%
トリスチレンフェノール+10~20モルEO 2%
1,2-ベンズイソチアゾリン-3-オン(20%水溶液の形態) 0.5%
モノアゾ顔料カルシウム塩 5%
シリコーン油(75 %水中エマルジョンの形態) 0.2%
水 45.3%
28部の式(I)の化合物の組み合わせを、2部の芳香族溶剤及び7部のトルエンジイソシアネート/ポリメチレン-ポリフェニルイソシアネート混合物(8:1)と混合する。この混合物を、1.2部のポリビニルアルコール、0.05部の脱泡剤及び51.6部の水の混合物中で、所望の粒径が達成されるまで乳化させる。このエマルジョンに、2.8部の1,6-ジアミノヘキサンの5.3部の水中の混合物を添加する。この混合物を重合反応が完了するまで撹拌する。
℃=摂氏度
CDCl3=クロロホルム-d
d=二重項
Pd2(dba)3 =トリス(ジベンジリデンアセトン)ジパラジウム(0)
DIPEA=N,N-ジイソプロピルエチルアミン
DMF=ジメチルホルムアミド
HATU=1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム3-オキシドヘキサフルオロリン酸
m=多重項
MHz=メガヘルツ
mp=融点
N=ノルマル
ppm=百万分率
q=四重項
s=一重項
t=三重項
THF=テトラヒドロフラン
キサントホス =4,5-ビス(ジフェニルホスフィノ)-9,9-ジメチルキサンテン
a)メチル2-[(2,6-ジフルオロ-4-ピリジル)アミノ]-5-メチル-チアゾール-4-カルボキシレートの調製
方法A:Waters製ACQUITY UPLC、Waters UPLC HSS T3、粒径1.8μm、30×2.1mmのカラム、0.85mL/分、60℃、H2O/MeOH 95:5+0.05% HCOOH(90%)/CH3CN+0.05% HCOOH(10%)-1.2分-CH3CN+0.05% HCOOH(100%)-0.30分、Waters製ACQUITY SQD質量分光計、イオン化法:エレクトロスプレー(ESI)、極性:陽イオン、キャピラリ(kV)3.00、コーン(V)30.00、抽出器(V)2.00、ソース温度(℃)150、脱溶剤温度(℃)350、コーンガス流(L/Hr)0、脱溶剤ガス流(L/Hr)650)。
機器パラメータ:イオン化法:エレクトロスプレー極性:陽(陰)イオンキャピラリ(kV)3.00、コーン(V)30.00、抽出器(V)2.00、ガス温度(℃)350、乾燥ガス流(mL/分)9.8、ネブライザ圧力45psig、質量範囲:90~1000Da。
HPLC:Agilent製HP 1100 HPLC:溶剤デガッサ、クォータナリーポンプ(ZCQ)/バイナリポンプ(ZDQ)、被加熱カラムコンパートメント及びダイオード-アレイ検出器。カラム:porpshell 120 C18、2.7μm粒径、120Å、4.6×50mm、温度:30℃。DAD波長範囲(nm):190~400溶剤勾配:A=水+0.1% HCOOH。B=アセトニトリル+0.08% HCOOH。移動相:
HPLC:株式会社島津製作所製LC-20A。カラム:Dikma、DiamonsilC18(2)(5μm、150×4.6mm)。
移動相A:H2O(0.1%TFAを添加);移動相B:ACN(0.1%TFAを添加)。流量:1.0ml/分
検出:UV@254nm。オーブン温度:40℃。移動相:
オクタノール-水分配係数(LogPと表記)を、オクタノールでコーティングした逆相小型カラムを用いるHPLC法により計測した。分配係数Pは、HPLC保持因子に正比例する。この方法に係る一般原則は、例えばJ.Pharm.Sci.,67(1978)1364-7に記載されている。
光安定性テストは、太陽光のスペクトル及び強度を再現するフィルタ補正したキセノンランプシステム(Atlas Suntest)を用いて、ガラス表面上への化合物及び配合物の薄いフィルム状の沈着物に照射することにより行った。Suntestのスペクトル出力は、正午での、典型的な一日における最高照射レベル(UK、真夏)である750W/m2にセットした。
テスト化合物の飽和溶液を、緩衝剤水溶液(10mM混合リン酸塩、pH7.20)又はヘプタン中において調製した。典型的には、1mLの緩衝剤又はヘプタンを含む、2本のドラムバイアル中の1mgのテスト化合物を、最初に超音波浴中に20分間置いた後、ローラ振盪機において一晩(20時間)放置した。次いで、飽和サンプルをMillex-HV 0.45ミクロンシリンジフィルタ(溶剤に応じて水性又は非水性版)でろ過した。次いで、水性サンプルをLCMSへ直接注入することで分析し、PDA検出を用いるピーク面積を既知の濃度を有する標準(ヘプタンサンプルを先ず乾燥させ、LCに適合する溶剤、典型的には30:70アセトニトリル:0.2%ギ酸に再度溶解させた)と比較した。プロトコルの差として、溶解度がきわめて低いことが予期される化合物についてはフィルタを事前に飽和させ、及び、油については飽和サンプルの遠心分離を行った。
実施例B1:アルテルナリア ソラニ(Alternaria solani)/トマト/葉片(夏疫病)
トマト葉片(cv.Baby)を、マルチウェルプレート(24ウェル型)中の寒天上に置き、水で希釈した配合されたテスト化合物を噴霧する。適用から2日後に、葉片に、真菌の胞子懸濁液を播種する。播種した葉片を、気候キャビネット中において、12/12時間(明/暗)の光環境下に、23℃/21℃(昼/夜)及び80%(rh)でインキュベートし、化合物の活性を、適切なレベルの病害による損傷が未処理の検査用葉片に現れた時点で(適用から5~7日後)、未処理のものと比した病害防除として評価する。
極低温保管しておいた真菌の分生子を栄養液体培地(Vogels液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌の芽胞を含有する栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から3~4日間後に、成長の阻害を測光法により測定する。
極低温保管しておいた真菌の分生子を栄養液体培地(PDBジャガイモブドウ糖液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌の芽胞を含有する栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から3~4日間後に、成長の阻害を測光法により計測する。
コムギ葉の一部(cv.Kanzler)をマルチウェルプレート(24ウェル型)中の寒天上に置き、水で希釈した配合されたテスト化合物を噴霧する。適用から1日後に、ウドンコ病に感染した植物をテストプレート上で振ることにより葉片に播種した。播種した葉片を、気候チャンバ中において、24時間の暗闇、これに続く、12時間の光/12時間の暗闇の光環境下に、20℃及び60%の相対湿度でインキュベートし、この化合物の活性を、適切なレベルの病害による損傷が未処理の検査用葉の一部に現れた時点で(適用から6~8日後)、未処理のものと比した病害防除として評価する。
コムギ小穂(cv.Monsun)をマルチウェルプレート(24ウェル型)中の寒天の上に載せ、水で希釈した配合したテスト化合物を噴霧する。適用から1日後に、小穂を真菌の胞子懸濁液で播種する。気候室中において、72時間の半暗闇、これに続く、12時間の光/12時間の暗闇の光環境下、20℃及び60%の相対湿度で播種した小穂をインキュベートし、化合物の活性を、適切なレベルの病害による損傷が未処理の検査用小穂に現れた時点で(適用から6~8日間)、未処理のものと比した病害防除割合として評価する。
コムギ小穂(cv.Monsun)をマルチウェルプレート(24ウェル型)中の寒天の上に載せ、水で希釈した配合したテスト化合物を噴霧する。適用から1日後に、小穂を真菌の胞子懸濁液で播種する。気候室中において、72時間の半暗闇、これに続く、12時間の光/12時間の暗闇の光環境下、20℃及び60%の相対湿度で播種したテスト葉片をインキュベートし、化合物の活性を、適当なレベルの病害による損傷が未処理の検査用小穂に現れた時点で(適用から6~8日間)、未処理のものと比した病害防除割合として評価する。
コムギの葉の断片(cv.Kanzler)をマルチウェルプレート(24ウェル型)中の寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。葉片に、適用から2日後に、真菌の胞子懸濁液を播種する。播種されたテスト葉片を、20℃及び75% rhで、12時間の明かり/12時間の暗闇の光環境下に、人工気候室中においてインキュベートし、適切なレベルの病害が未処理の検査用葉片において現れる場合(適用から5~7日後)、化合物の活性度を未処理のものと比した病害の防除割合として評価する。
極低温保管しておいた真菌の分生子を栄養液体培地(PDBジャガイモブドウ糖液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌の芽胞を含有する栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から4~5日間後に、成長の阻害を測光法により測定する。
極低温保管しておいた真菌の分生子を栄養液体培地(PDBジャガイモブドウ糖液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌の芽胞を含有する栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から4~5日間後に、成長の阻害を測光法により測定する。
ダイズ葉片をマルチウェルプレート(24ウェル型)中の水寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。適用から1日後に、葉の裏面に胞子懸濁液を吹付けることにより葉片に播種する。人工気候室中、暗闇で、20℃及び75% rhにおける24~36時間のインキュベーション期間の後、葉片を、12時間の明かり/日及び75% rhで、20℃で保持する。化合物の活性を、適切なレベルの病害が未処理の検査用葉片に現れた時点で(適用から12~14日後)、未処理のものと比した病害防除割合として評価する。
ブドウの葉片をマルチウェルプレート(24ウェル型)中の水寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。葉片に、適用から1日後に、真菌の胞子懸濁液を播種する。気候キャビネット中において、12時間の明かり/12時間の暗闇の光環境下に、19℃及び80%の相対湿度で播種した葉片をインキュベートし、化合物の活性を、未処理の検査用葉片に適切なレベルの病害による損傷が現れた時点(適用から6~8日後)で、未処理のものと比した病害防除として評価する。
コムギの葉の断片(cv.Kanzler)をマルチウェルプレート(24ウェル型)中の寒天上に置く。葉の断片に真菌の胞子懸濁液を播種する。プレートは、暗中に、19℃及び75% rhで保管する。水中に希釈した配合したテスト化合物を播種の1日後に適用する。葉の断片を、19℃及び75% rhで、12時間の明かり/12時間の暗闇の光環境下に、人工気候室中においてインキュベートし、適切なレベルの病害が未処理の検査用葉の断片において現れる場合(適用から6~8日後)、化合物の活性度を未処理のものと比した病害の防除割合として評価する。
コムギの葉の断片(cv.Kanzler)をマルチウェルプレート(24ウェル型)中の寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。葉片に、適用から1日後に、真菌の胞子懸濁液を播種する。播種した葉の断片を、19℃及び75% rhで、12時間の明かり/12時間の暗闇の光環境下に、人工気候室中においてインキュベートし、化合物の活性を、適切なレベルの病害が未処理の検査用葉の断片に現れた時点で(適用から7~9日後)、未処理のものと比した病害防除割合として評価する。
イネの葉の断片(cv.Ballila)をマルチウェルプレート(24ウェル型)中の寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。葉の断片に、適用から2日後に、真菌の胞子懸濁液を播種する。播種した葉の断片を、22℃及び80% rhで、24時間の暗闇、続いて、12時間の明かり/12時間の暗闇の光環境下に、人工気候室中においてインキュベートし、化合物の活性を、適切なレベルの病害が未処理の検査用葉の断片に現れた時点で(適用から5~7日後)、未処理のものと比した病害防除割合として評価する。
オオムギの葉の断片(cv.Hasso)をマルチウェルプレート(24ウェル型)中の寒天上に置き、水中に希釈した配合したテスト化合物を噴霧する。葉の断片に、適用から2日後に、真菌の胞子懸濁液を播種する。播種した葉の断片を、20℃及び65% rhで、12時間の明かり/12時間の暗闇の光環境下に、人工気候室中においてインキュベートし、化合物の活性を、適切なレベルの病害が未処理の検査用葉の断片に現れた時点で(適用から5~7日後)、未処理のものと比して病害防除として評価する。
新たに増殖させた液体培養の真菌の菌糸体断片を、栄養液体培地(PDBジャガイモブドウ糖液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌材料を含む栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から3~4日間後に、成長の阻害を測光法により測定する。
極低温保管しておいた真菌の分生子を栄養液体培地(PDBジャガイモブドウ糖液体培地)に直接混合する。テスト化合物の(DMSO)溶液をマイクロタイタープレート(96ウェル型)に入れた後、真菌の芽胞を含有する栄養液体培地を加える。テストプレートを24℃でインキュベートし、適用から4~5日間後に、成長の阻害を測光法により測定する。
Claims (15)
- 式(I)の化合物:
YはC-F、C-H又はNであり;
R1は、水素、C1~C6アルキル、C1~C6アルコキシ、C1~C6ハロアルキル、C1~C6ヒドロキシアルキル、C1~C6アルコキシC1~C6アルキル、C3~C6シクロアルキル、C1~C6アルコキシC1~C3アルコキシ、C1~C6アルコキシカルボニル、C1~C6アルコキシカルボニルC1~C4アルキル、C1~C6アルコキシカルボニルオキシC1~C4アルキル、C1~C6アルキルカルボニルオキシC1~C4アルキル、C2~C6アルケニルオキシ、C2~C6アルキニルオキシ、C1~C6アルキルスルファニル、ジ(C1~C6アルキル)アミノ、フェニル、フェニルC1~C3アルキル、フェニルC1~C3アルコキシC1~C3アルキル、フェノキシ又はヘテロアリール(ここで、前記ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1又は2個のヘテロ原子を含む5員又は6員芳香族単環式環である)であり;
R2は、水素、ハロゲン、シアノ、C1~C4アルキル、C1~C4アルコキシ、C1~C4ハロアルキル又はHC(O)NH-であり;
R3は、C1~C8アルキル、C1~C8ハロアルキル、C1~C8アルコキシ、C3~C8シクロアルキル、C3~C8シクロアルキルC1~C2アルキル(ここで、前記シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)、フェニル、フェニルC1~C2アルキル、ヘテロアリール、ヘテロアリールC1~C2アルキル(ここで、前記ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1、2、3又は4個のヘテロ原子を含む5員又は6員芳香族単環式環である)、ヘテロシクリル、ヘテロシクリルC1~C2アルキル(ここで、前記ヘテロシクリルは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む4員、5員又は6員非芳香族単環式環である)、又は、窒素、酸素及び硫黄から独立して選択される1、2、3、4又は5個のヘテロ原子を任意選択により含む5員~10員非芳香族スピロ環式カルボジ-又はカルボトリ-シクリル環系であり、ここで、前記スピロ環式カルボジ-又はカルボトリ-シクリル環系は各々、C1~C2アルキレンリンカーを介して分子の残部に任意選択により結合しており;
R4は、ハロゲン、C1~C4アルキル、C1~C4アルコキシ又はC1~C4ハロアルキルであり;
XはN又はC-Hである)
又は、その塩若しくはN-オキシド。 - R1は、水素、C1~C4アルキル、C1~C4アルコキシ、C1~C4ハロアルキル、C1~C4ヒドロキシアルキル、C1~C3アルコキシC1~C4アルキル、C3~C6シクロアルキル、C1~C4アルコキシC1~C3アルコキシ、C1~C3アルコキシカルボニル、C1~C3アルコキシカルボニルC1~C4アルキル、C1~C4アルコキシカルボニルオキシC1~C3アルキル、C1~C4アルキルカルボニルオキシC1~C3アルキル、C3~C5アルキニルオキシ、C1~C4アルキルスルファニル、ジ(C1~C4アルキル)アミノ、フェニル、フェニルC1~C3アルキル、フェニルC1~C3アルコキシC1~C3アルキル、フェノキシ又はヘテロアリール(ここで、前記ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1又は2個のヘテロ原子を含む5員又は6員芳香族単環式環である)である、請求項1に記載の化合物。
- R1は、水素、C1~C3アルキル、C1~C3アルコキシ、C1~C3ハロアルキル、C1~C3ヒドロキシアルキル、メトキシC1~C4アルキル、C3~C4シクロアルキル、C1~C2アルコキシC1~C2アルコキシ、C1~C3アルコキシカルボニル、メトキシカルボニルC1~C3アルキル、C1~C2アルコキシカルボニルオキシC1~C2アルキル、C1~C2アルキルカルボニルオキシC1~C2アルキル、C3~C4アルキニルオキシ、C1~C3アルキルスルファニル、ジエチルアミノ、フェニル、ベンジル、フェノキシ、ベンジルオキシC1~C2アルキル又はヘテロアリール(ここで、前記ヘテロアリールは、酸素及び硫黄から選択される1個のヘテロ原子を含む5員又は6員芳香族単環式環である)である、請求項1又は請求項2に記載の化合物。
- R1は、水素、メチル、エチル、メトキシ、エトキシ、フルオロメチル、クロロメチル、ブロモメチル、2,2,2-トリフルオロエチル、1-ヒドロキシエチル、メトキシメチル、1-メトキシエチル、1-エトキシメチル、1-メトキシ-1-メチルエチル、シクロプロピル、メトキシエトキシ、エトキシカルボニル、2-メトキシ-2-オキソ-エチル、2-メトキシ-オキソ-エチル、2-メトキシ-オキソ-プロピル、プロパルギルオキシ、1-メトキシカルボニルオキシ-エチル、1-エトキシカルボニルオキシ-エチル、1-メチルカルボニルオキシ-エチル、メチルカルボニルオキシメチル、メチルスルファニル、エチルスルファニル、イソプロピルスルファニル、ジエチルアミノ、フェニル、ベンジル、フェノキシ、ベンジルオキシメチル、1-ベンジルオキシエチル、2-フラニル、又は2-チオフェニルである、請求項1~3のいずれか一項に記載の化合物。
- R2がハロゲン、C1-C2アルキル、C1-C2アルコキシ又はHC(O)NH-である、請求項1~4のいずれか一項に記載の化合物。
- R2がメチルである、請求項1~5のいずれか一項に記載の化合物。
- R3は、C1~C4アルキル、C1~C3アルコキシ、C3~C6シクロアルキル、C3~C6シクロアルキルC1~C2アルキル(ここで、前記シクロアルキル基は、R4により表される1~3個の基で任意選択により置換されている)、フェニル、ヘテロアリール(ここで、前記ヘテロアリールは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む5員又は6員芳香族単環式環である)、ヘテロシクリル(ここで、前記ヘテロシクリルは、窒素、酸素及び硫黄から独立して選択される1、2又は3個のヘテロ原子を含む4員、5員又は6員非芳香族単環式環である)、又は、窒素、酸素及び硫黄から選択される1個のヘテロ原子を任意選択により含む5員~12員非芳香族スピロ環式カルボジ-又はカルボトリ-シクリル環系である、請求項1~6のいずれか一項に記載の化合物。
- R3はC3~C4シクロアルキル(ここで、前記シクロアルキル基は、R4によって表される1又は2個の基で任意選択により置換されている)であるか、又は、R3は6員~8員非芳香族スピロ環式カルボジ-シクリル環系である、請求項1~7のいずれか一項に記載の化合物。
- XはNである、請求項1~8のいずれか一項に記載の化合物。
- YはC-Fである、請求項1~9のいずれか一項に記載の化合物。
- R3は、シクロブチル、2,2-ジメチルシクロブチル又はスピロ[3.4]オクタニルである、請求項1~10のいずれか一項に記載の化合物。
- 請求項1~11のいずれか一項に記載の殺菌・殺カビ的に有効な量の式(I)の化合物を含む農薬組成物。
- 少なくとも1種の追加の活性処方成分及び/又は農芸化学的に許容される希釈剤又はキャリアをさらに含む、請求項12に記載の組成物。
- 植物病原性微生物による有用な植物の外寄生を防除又は予防する方法であって、殺菌・殺カビ的に有効な量の請求項1~11のいずれか一項に記載の式(I)の化合物、又は、活性処方成分としてこの化合物を含む組成物を、前記植物、その一部又はその生息地に適用する、方法。
- 殺菌・殺カビ剤としての請求項1~11のいずれか一項に記載の式(I)の化合物の使用。
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AR117183A1 (es) | 2021-07-14 |
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BR112021010365A2 (pt) | 2021-08-24 |
EP3887361A1 (en) | 2021-10-06 |
CA3119725A1 (en) | 2020-06-04 |
UY38490A (es) | 2020-06-30 |
KR20210098973A (ko) | 2021-08-11 |
MX2021006050A (es) | 2021-07-06 |
TW202039480A (zh) | 2020-11-01 |
AU2019386994A1 (en) | 2021-06-03 |
CO2021007059A2 (es) | 2021-06-10 |
CL2021001362A1 (es) | 2021-11-12 |
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