UA97533C2 - Амидиновые производные n-циклоалкилбензила, фунгицидная композиция на их основе и способ борьбы с фитопатогенными грибами культур - Google Patents

Амидиновые производные n-циклоалкилбензила, фунгицидная композиция на их основе и способ борьбы с фитопатогенными грибами культур Download PDF

Info

Publication number: UA97533C2
Authority: UA; Ukraine
Prior art keywords: different; same; alkyl; halogen atoms; hydrogen atom
Prior art date: 2007-07-31

Application number

UAA201000816A

Other languages

English (en)

Ukrainian (uk)

Inventor

Филип Деборде

Стефан Гари

Мари-Клер Гросжан-Курноер

Бенуа Хартманн

Филип Ринольфи

Жан-Пьер Ворс

Original Assignee

Байер Кропсайнс Аг

Priority date (The priority date 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 date listed.)

2007-07-31

Filing date

2008-07-31

Publication date

2012-02-27

2008-07-31 Application filed by Байер Кропсайнс Аг filed Critical Байер Кропсайнс Аг

2012-02-27 Publication of UA97533C2 publication Critical patent/UA97533C2/ru

Links

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238000000034 method Methods 0.000 title claims abstract description 46
230000000855 fungicidal effect Effects 0.000 title claims abstract description 14
241000233866 Fungi Species 0.000 title claims abstract description 8
230000003032 phytopathogenic effect Effects 0.000 title claims abstract description 6
239000000417 fungicide Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 83
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
125000001424 substituent group Chemical group 0.000 claims abstract description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims description 189
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 74
-1 pyridinyloxy Chemical group 0.000 claims description 41
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
235000013399 edible fruits Nutrition 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
231100001184 nonphytotoxic Toxicity 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
239000002689 soil Substances 0.000 claims description 3
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
150000001409 amidines Chemical class 0.000 claims 7
125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims 1
125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
125000005103 alkyl silyl group Chemical group 0.000 claims 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
150000001408 amides Chemical class 0.000 abstract description 7
239000013543 active substance Substances 0.000 abstract description 2
241000196324 Embryophyta Species 0.000 description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000003112 inhibitor Substances 0.000 description 13
229910052796 boron Inorganic materials 0.000 description 11
201000010099 disease Diseases 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
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238000005507 spraying Methods 0.000 description 11
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239000011149 active material Substances 0.000 description 10
239000002585 base Substances 0.000 description 10
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229920000136 polysorbate Polymers 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
241000221785 Erysiphales Species 0.000 description 8
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229910052784 alkaline earth metal Inorganic materials 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
239000002023 wood Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
240000005979 Hordeum vulgare Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
241000894007 species Species 0.000 description 6
239000000725 suspension Substances 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000000265 homogenisation Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000758 substrate Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
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 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
241000223218 Fusarium Species 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000012545 processing Methods 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
201000002909 Aspergillosis Diseases 0.000 description 3
208000036641 Aspergillus infections Diseases 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
ZGIWASKEQCJBME-UHFFFAOYSA-N N-methylidenepyridine-2-carbothioamide Chemical class C=NC(=S)C1=CC=CC=N1 ZGIWASKEQCJBME-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
125000001841 imino group Chemical group [H]N=* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
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PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
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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 2
XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 2
JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 2
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241000223600 Alternaria Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
239000005790 Fosetyl Substances 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
239000005799 Isopyrazam Substances 0.000 description 2
240000008415 Lactuca sativa Species 0.000 description 2
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208000031888 Mycoses Diseases 0.000 description 2
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000233614 Phytophthora Species 0.000 description 2
239000005821 Propamocarb Substances 0.000 description 2
244000088415 Raphanus sativus Species 0.000 description 2
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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230000009418 agronomic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
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229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
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 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 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
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
150000001793 charged compounds Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000010949 copper Substances 0.000 description 2
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229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-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
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
229960002125 enilconazole Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000002262 irrigation Effects 0.000 description 2
238000003973 irrigation Methods 0.000 description 2
MKARNSWMMBGSHX-UHFFFAOYSA-N m-xylylamine Natural products CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical group NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
JGCSKOVQDXEQHI-UHFFFAOYSA-N phenazine-1-carboxylic acid Chemical compound C1=CC=C2N=C3C(C(=O)O)=CC=CC3=NC2=C1 JGCSKOVQDXEQHI-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
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CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 1
ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
229960002132 pyrrolnitrin Drugs 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
208000005687 scabies Diseases 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
IHTAIAZIELSSOO-MKWAYWHRSA-N sodium (Z)-hydroxyimino-(1-hydroxypropan-2-yl)-oxidoazanium Chemical compound [Na+].CC(CO)[N+](\[O-])=N\O IHTAIAZIELSSOO-MKWAYWHRSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000004528 solution for seed treatment Substances 0.000 description 1
238000001228 spectrum Methods 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
239000003381 stabilizer Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
229960005322 streptomycin Drugs 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
239000004546 suspension concentrate Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 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
XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
229960002722 terbinafine Drugs 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
235000010296 thiabendazole Nutrition 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
239000002562 thickening agent Substances 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
238000007280 thionation reaction Methods 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
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000014616 translation Effects 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
201000008297 typhoid fever Diseases 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
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
229960004740 voriconazole Drugs 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000004565 water dispersible tablet Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
241000228158 x Triticosecale Species 0.000 description 1
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A01N43/80—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 1,2
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/16—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

UAA201000816A 2007-07-31 2008-07-31 Амидиновые производные n-циклоалкилбензила, фунгицидная композиция на их основе и способ борьбы с фитопатогенными грибами культур UA97533C2 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP07356104		2007-07-31
PCT/EP2008/060039 WO2009016220A1 (en)	2007-07-31	2008-07-31	Fungicidal n-cycloalkyl-benzyl-thiocarboxamides or n-cycloalkyl-benzyl-n' -substituted-amidine derivatives

Publications (1)

Publication Number	Publication Date
UA97533C2 true UA97533C2 (ru)	2012-02-27

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UAA201000816A UA97533C2 (ru)	2007-07-31	2008-07-31	Амидиновые производные n-циклоалкилбензила, фунгицидная композиция на их основе и способ борьбы с фитопатогенными грибами культур

Country Status (17)

Country	Link
US (1)	US8410157B2 (ru)
EP (1)	EP2182800B1 (ru)
JP (1)	JP5356383B2 (ru)
CN (1)	CN101820759B (ru)
AT (1)	ATE499835T1 (ru)
AU (1)	AU2008281772B2 (ru)
BR (1)	BRPI0813044B1 (ru)
CA (1)	CA2692767C (ru)
CO (1)	CO6160263A2 (ru)
DE (1)	DE602008005320D1 (ru)
ES (1)	ES2359877T3 (ru)
MX (1)	MX2010001004A (ru)
PT (1)	PT2182800E (ru)
RU (1)	RU2480457C2 (ru)
UA (1)	UA97533C2 (ru)
WO (1)	WO2009016220A1 (ru)
ZA (1)	ZA200908563B (ru)

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UA100291C2 (ru)	2008-08-01	2012-12-10	Байєр Кропсайнс Аг	Фунгицидные производные n-циклоалкил-n-бифенилметилкарбоксамида
AR076839A1 (es) *	2009-05-15	2011-07-13	Bayer Cropscience Ag	Derivados fungicidas de pirazol carboxamidas
EP2251331A1 (en)	2009-05-15	2010-11-17	Bayer CropScience AG	Fungicide pyrazole carboxamides derivatives
AU2011260333B2 (en)	2010-06-03	2014-07-24	Bayer Cropscience Ag	N-[(het)arylalkyl)] pyrazole (thio)carboxamides and their heterosubstituted analogues
EP3181550B1 (en)	2010-07-20	2019-11-20	Bayer Intellectual Property GmbH	Benzocycloalkenes as antifungal agents
EP2630125B1 (en)	2010-10-21	2016-08-24	Bayer Intellectual Property GmbH	N-benzyl heterocyclic carboxamides
KR20130116074A (ko)	2010-11-02	2013-10-22	바이엘 인텔렉쳐 프로퍼티 게엠베하	Ｎ-헤타릴메틸 피라졸릴카르복사미드
KR101974228B1 (ko) *	2011-04-22	2019-04-30	바이엘 크롭사이언스 악티엔게젤샤프트	(티오)카르복사미드 유도체 및 살충 또는 살비 또는 살선충 활성 화합물을 함유하는 활성 화합물 배합물
HUE026627T2 (en) *	2011-04-22	2016-06-28	Bayer Ip Gmbh	Combinations of an active ingredient comprising a carboxamide derivative and a fungicide compound
US9374998B2 (en)	2012-03-26	2016-06-28	Bayer Intellectual Property Gmbh	N-cycloalkyl-N-[(cycloalkenylphenyl)methylene]-(thio)carboxamide derivatives
CN104428294B (zh)	2012-04-20	2017-07-14	拜尔农科股份公司	N‑环烷基‑n‑[(杂环基苯基)亚甲基]‑(硫代)羧酰胺衍生物
EP2838363A1 (en) *	2012-04-20	2015-02-25	Bayer Cropscience AG	N-cycloalkyl-n-[(trisubstitutedsilylphenyl)methylene]-(thio)carboxamide derivatives
DK2908641T3 (da)	2012-10-19	2018-04-23	Bayer Cropscience Ag	Fremgangsmåde til behandling af planter mod svampe, der er resistente over for fungicider, ved anvendelse af carboxamid- eller thiocarboxamidderivater
CA2888556C (en)	2012-10-19	2020-07-07	Bayer Cropscience Ag	Method of plant growth promotion using carboxamide derivatives
US20150250176A1 (en)	2012-10-19	2015-09-10	Bayer Cropscience Ag	Method for enhancing tolerance to abiotic stress in plants using carboxamide or thiocarboxamide derivatives
CN105357968A (zh)	2012-10-19	2016-02-24	拜尔农科股份公司	包含羧酰胺衍生物的活性化合物复配物
BR112015008802B1 (pt)	2012-10-19	2020-11-10	Bayer Cropscience Ag	composições ativas, método para controlar fungos fitopatogênicos e uso das referidas composições ativas
US10098350B2 (en)	2013-04-15	2018-10-16	E. I. Du Pont De Nemours And Company	Fungicidal amides
EP3013802B1 (en) *	2013-06-26	2019-08-14	Bayer Cropscience AG	N-cycloalkyl-n-[(bicyclylphenyl)methylene]-(thio)carboxamide derivatives
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2008
- 2008-07-31 EP EP08786664A patent/EP2182800B1/en not_active Not-in-force
- 2008-07-31 ES ES08786664T patent/ES2359877T3/es active Active
- 2008-07-31 PT PT08786664T patent/PT2182800E/pt unknown
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- 2008-07-31 JP JP2010518673A patent/JP5356383B2/ja not_active Expired - Fee Related
- 2008-07-31 CN CN200880101350XA patent/CN101820759B/zh not_active Expired - Fee Related
- 2008-07-31 AT AT08786664T patent/ATE499835T1/de not_active IP Right Cessation
- 2008-07-31 AU AU2008281772A patent/AU2008281772B2/en not_active Ceased
- 2008-07-31 BR BRPI0813044A patent/BRPI0813044B1/pt not_active IP Right Cessation
- 2008-07-31 UA UAA201000816A patent/UA97533C2/ru unknown
- 2008-07-31 DE DE602008005320T patent/DE602008005320D1/de active Active
- 2008-07-31 WO PCT/EP2008/060039 patent/WO2009016220A1/en active Application Filing
- 2008-07-31 RU RU2010107171/04A patent/RU2480457C2/ru not_active IP Right Cessation
- 2008-07-31 MX MX2010001004A patent/MX2010001004A/es active IP Right Grant
- 2008-07-31 US US12/452,925 patent/US8410157B2/en not_active Expired - Fee Related
2009
- 2009-12-02 ZA ZA200908563A patent/ZA200908563B/xx unknown
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Also Published As

Publication number	Publication date
RU2010107171A (ru)	2011-09-10
CN101820759B (zh)	2013-12-25
PT2182800E (pt)	2011-05-16
CN101820759A (zh)	2010-09-01
BRPI0813044B1 (pt)	2017-03-21
CA2692767C (en)	2016-02-09
DE602008005320D1 (de)	2011-04-14
EP2182800B1 (en)	2011-03-02
US20100144817A1 (en)	2010-06-10
US8410157B2 (en)	2013-04-02
CA2692767A1 (en)	2009-02-05
ES2359877T3 (es)	2011-05-27
ZA200908563B (en)	2010-08-25
CO6160263A2 (es)	2010-05-20
WO2009016220A1 (en)	2009-02-05
AU2008281772A1 (en)	2009-02-05
ATE499835T1 (de)	2011-03-15
JP5356383B2 (ja)	2013-12-04
MX2010001004A (es)	2010-03-09
EP2182800A1 (en)	2010-05-12
RU2480457C2 (ru)	2013-04-27
AU2008281772B2 (en)	2013-05-30
JP2010534715A (ja)	2010-11-11
BRPI0813044A2 (pt)	2014-10-07

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