MXPA04009002A

MXPA04009002A - Piridinilamidas fusionadas, biciclicas y composiciones ventajosas de las mismas para uso como fungicidas.

Piridinilamidas fusionadas, biciclicas y composiciones ventajosas de las mismas para uso como fungicidas.

Info

Publication number: MXPA04009002A
Authority: MX; Mexico
Prior art keywords: carbon atoms; compound; group; compounds; formula
Prior art date: 2002-03-19

Application number

MXPA04009002A

Other languages

English (en)

Spanish (es)

Inventor

Alan Clark David

Original Assignee

Du Pont

Priority date

2002-03-19

Filing date

2003-02-20

Publication date

2004-12-07

2003-02-20 Application filed by Du Pont filed Critical Du Pont

2004-12-07 Publication of MXPA04009002A publication Critical patent/MXPA04009002A/es

Links

239000000203 mixture Substances 0.000 title claims abstract description 121
239000000417 fungicide Substances 0.000 title claims description 48
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 title description 3
125000002619 bicyclic group Chemical group 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 242
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 219
201000010099 disease Diseases 0.000 claims abstract description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
229910052799 carbon Inorganic materials 0.000 claims abstract description 23
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 21
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
125000004429 atom Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
150000001204 N-oxides Chemical class 0.000 claims abstract description 7
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
125000001188 haloalkyl group Chemical group 0.000 claims description 21
125000001309 chloro group Chemical group Cl* 0.000 claims description 19
125000004438 haloalkoxy group Chemical group 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
229930182558 Sterol Natural products 0.000 claims description 15
150000003432 sterols Chemical class 0.000 claims description 15
235000003702 sterols Nutrition 0.000 claims description 15
125000004414 alkyl thio group Chemical group 0.000 claims description 14
OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 13
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000004995 haloalkylthio group Chemical group 0.000 claims description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
230000000855 fungicidal effect Effects 0.000 claims description 10
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 10
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
230000002538 fungal effect Effects 0.000 claims description 9
125000000262 haloalkenyl group Chemical group 0.000 claims description 9
125000000232 haloalkynyl group Chemical group 0.000 claims description 9
230000006540 mitochondrial respiration Effects 0.000 claims description 9
244000052769 pathogen Species 0.000 claims description 9
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
230000006696 biosynthetic metabolic pathway Effects 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
102000004190 Enzymes Human genes 0.000 claims description 7
108090000790 Enzymes Proteins 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 claims description 6
102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 claims description 6
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
239000012990 dithiocarbamate Substances 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 5
125000005543 phthalimide group Chemical class 0.000 claims description 5
150000003053 piperidines Chemical class 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
230000027756 respiratory electron transport chain Effects 0.000 claims description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
125000006574 non-aromatic ring group Chemical group 0.000 claims description 3
230000001717 pathogenic effect Effects 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
244000000004 fungal plant pathogen Species 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 547
-1 n- propyl Chemical group 0.000 description 55
229940125898 compound 5 Drugs 0.000 description 40
229940126214 compound 3 Drugs 0.000 description 38
238000012360 testing method Methods 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
241000196324 Embryophyta Species 0.000 description 24
239000000725 suspension Substances 0.000 description 20
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
239000003085 diluting agent Substances 0.000 description 16
XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 15
239000005802 Mancozeb Substances 0.000 description 15
239000004480 active ingredient Substances 0.000 description 15
239000005756 Cymoxanil Substances 0.000 description 14
238000009472 formulation Methods 0.000 description 14
PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 13
239000005772 Famoxadone Substances 0.000 description 13
239000005807 Metalaxyl Substances 0.000 description 13
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 13
239000005789 Folpet Substances 0.000 description 12
HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 12
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 12
229920000940 maneb Polymers 0.000 description 12
239000004094 surface-active agent Substances 0.000 description 12
239000005730 Azoxystrobin Substances 0.000 description 11
239000005857 Trifloxystrobin Substances 0.000 description 11
WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 11
239000003112 inhibitor Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
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 11
239000005800 Kresoxim-methyl Substances 0.000 description 10
239000005823 Propineb Substances 0.000 description 10
239000005869 Pyraclostrobin Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 10
KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 10
HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000005774 Fenamidone Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000011717 all-trans-retinol Substances 0.000 description 9
235000019169 all-trans-retinol Nutrition 0.000 description 9
LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 9
UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 7
239000005734 Benalaxyl Substances 0.000 description 7
239000005745 Captan Substances 0.000 description 7
244000061456 Solanum tuberosum Species 0.000 description 7
235000002595 Solanum tuberosum Nutrition 0.000 description 7
229940117949 captan Drugs 0.000 description 7
231100000676 disease causative agent Toxicity 0.000 description 7
239000007788 liquid Substances 0.000 description 7
CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 6
IXRUZEMDNAMNFO-UHFFFAOYSA-N 6-chloro-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4-one Chemical compound O=C1N(CCC)C(OCCC)=NC2=C1C=C(Cl)S2 IXRUZEMDNAMNFO-UHFFFAOYSA-N 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241000233622 Phytophthora infestans Species 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000009471 action Effects 0.000 description 6
239000008187 granular material Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000000047 product Substances 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241000233866 Fungi Species 0.000 description 5
235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
240000003768 Solanum lycopersicum Species 0.000 description 5
229930182692 Strobilurin Natural products 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
235000009754 Vitis X bourquina Nutrition 0.000 description 4
235000012333 Vitis X labruscana Nutrition 0.000 description 4
240000006365 Vitis vinifera Species 0.000 description 4
235000014787 Vitis vinifera Nutrition 0.000 description 4
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 4
MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000006013 carbendazim Substances 0.000 description 4
JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229910000365 copper sulfate Inorganic materials 0.000 description 4
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000008188 pellet Substances 0.000 description 4
FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 3
PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 3
PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
239000005741 Bromuconazole Substances 0.000 description 3
239000005747 Chlorothalonil Substances 0.000 description 3
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 3
239000005750 Copper hydroxide Substances 0.000 description 3
239000005767 Epoxiconazole Substances 0.000 description 3
241000221785 Erysiphales Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005780 Fluazinam Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000005796 Ipconazole Substances 0.000 description 3
239000005797 Iprovalicarb Substances 0.000 description 3
NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 3
239000005868 Metconazole Substances 0.000 description 3
241001281803 Plasmopara viticola Species 0.000 description 3
239000005821 Propamocarb Substances 0.000 description 3
239000005822 Propiconazole Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000005839 Tebuconazole Substances 0.000 description 3
239000005859 Triticonazole Substances 0.000 description 3
125000003302 alkenyloxy group Chemical group 0.000 description 3
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