UA67734C2 - Похідні 1-арилпіразолу з пестицидними властивостями, пестицидна композиція, спосіб боротьби зі шкідниками та спосіб одержання похідних (варіанти) - Google Patents

Похідні 1-арилпіразолу з пестицидними властивостями, пестицидна композиція, спосіб боротьби зі шкідниками та спосіб одержання похідних (варіанти) Download PDF

Info

Publication number: UA67734C2
Authority: UA; Ukraine
Prior art keywords: formula; alkyl; compound; amino; trifluoromethylphenyl
Prior art date: 1996-12-24

Application number

UA99074126A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Девід Трідвей Маннінг

Майкл Пелат

Тей-Тіх Ву

Девід Уільям Хавкінс

Original Assignee

Авентіс Кропсайнс С.А.

Авентис Кропсайнс С.А.

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.)

1996-12-24

Filing date

1997-12-18

Publication date

2004-07-15

1997-12-18 Application filed by Авентіс Кропсайнс С.А., Авентис Кропсайнс С.А. filed Critical Авентіс Кропсайнс С.А.

2004-07-15 Publication of UA67734C2 publication Critical patent/UA67734C2/uk

Links

239000000575 pesticide Substances 0.000 title claims description 17
150000001875 compounds Chemical class 0.000 claims description 152
-1 1H-pyrazol-1-yl Chemical group 0.000 claims description 108
239000000203 mixture Substances 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 55
238000000034 method Methods 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 45
241000607479 Yersinia pestis Species 0.000 claims description 36
241001465754 Metazoa Species 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 24
241000238631 Hexapoda Species 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
230000000361 pesticidal effect Effects 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
208000015181 infectious disease Diseases 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
239000003513 alkali Substances 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004961 1-arylpyrazolyl group Chemical group 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
241000251539 Vertebrata <Metazoa> Species 0.000 claims description 5
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
XPEOQIUFBJRCKE-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XPEOQIUFBJRCKE-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
230000037396 body weight Effects 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
XGQWFTJEQSVRCK-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrazole-3-carbothioamide Chemical compound NC1=C(SC(F)(F)F)C(C(=S)N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XGQWFTJEQSVRCK-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
YZDYMQLXPYEYJF-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl YZDYMQLXPYEYJF-UHFFFAOYSA-N 0.000 claims description 2
LNWUAHJAKNEAMP-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl LNWUAHJAKNEAMP-UHFFFAOYSA-N 0.000 claims description 2
PNTBJOMCNZIYCO-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PNTBJOMCNZIYCO-UHFFFAOYSA-N 0.000 claims description 2
VWHMZLMRNVXPFA-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VWHMZLMRNVXPFA-UHFFFAOYSA-N 0.000 claims description 2
LTLCKYCNOOXPKO-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=CC=C(C(F)(F)F)C=C1Cl LTLCKYCNOOXPKO-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000001879 copper Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
238000007033 dehydrochlorination reaction Methods 0.000 claims description 2
238000006193 diazotization reaction Methods 0.000 claims description 2
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
238000004683 secondary electrospray ionisation mass spectroscopy Methods 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims 2
238000005804 alkylation reaction Methods 0.000 claims 2
230000032050 esterification Effects 0.000 claims 2
238000005886 esterification reaction Methods 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
ZTOXNAIRALLYRB-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br ZTOXNAIRALLYRB-UHFFFAOYSA-N 0.000 claims 1
CICWDLGVJKMEIX-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br CICWDLGVJKMEIX-UHFFFAOYSA-N 0.000 claims 1
QVTQIKJXDLMRMV-UHFFFAOYSA-N C(C)S(=O)CCCNBr Chemical compound C(C)S(=O)CCCNBr QVTQIKJXDLMRMV-UHFFFAOYSA-N 0.000 claims 1
229910052797 bismuth Inorganic materials 0.000 claims 1
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000004615 ingredient Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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238000005507 spraying Methods 0.000 description 10
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239000003795 chemical substances by application Substances 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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125000001424 substituent group Chemical group 0.000 description 4
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230000036541 health Effects 0.000 description 1
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150000003840 hydrochlorides Chemical class 0.000 description 1
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235000013980 iron oxide Nutrition 0.000 description 1
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IATZLNCRIIUXJM-UHFFFAOYSA-N methyl hept-2-ynoate Chemical compound CCCCC#CC(=O)OC IATZLNCRIIUXJM-UHFFFAOYSA-N 0.000 description 1
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ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
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QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
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229920002451 polyvinyl alcohol Polymers 0.000 description 1
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239000004800 polyvinyl chloride Substances 0.000 description 1
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239000011148 porous material Substances 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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244000000040 protozoan parasite Species 0.000 description 1
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239000008262 pumice Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
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VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
241000894007 species Species 0.000 description 1
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230000028070 sporulation Effects 0.000 description 1
230000007480 spreading Effects 0.000 description 1
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230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
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238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000002562 thickening agent Substances 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
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 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
238000001665 trituration Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
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230000003612 virological effect Effects 0.000 description 1
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239000003643 water by type Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- 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
- C07D231/18—One oxygen or sulfur atom
- 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

UA99074126A 1996-12-24 1997-12-18 Похідні 1-арилпіразолу з пестицидними властивостями, пестицидна композиція, спосіб боротьби зі шкідниками та спосіб одержання похідних (варіанти) UA67734C2 (uk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3388596P	1996-12-24	1996-12-24
PCT/EP1997/007116 WO1998028279A1 (en)	1996-12-24	1997-12-18	Pesticidal 1-aryl and pyridylpyrazole derivatives

Publications (1)

Publication Number	Publication Date
UA67734C2 true UA67734C2 (uk)	2004-07-15

Family

ID=21873029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA99074126A UA67734C2 (uk)	1996-12-24	1997-12-18	Похідні 1-арилпіразолу з пестицидними властивостями, пестицидна композиція, спосіб боротьби зі шкідниками та спосіб одержання похідних (варіанти)

Country Status (19)

Country	Link
EP (1)	EP0948487A1 (id)
JP (1)	JP2001506665A (id)
KR (1)	KR20000062318A (id)
AP (1)	AP1004A (id)
AU (1)	AU747450B2 (id)
BG (1)	BG103592A (id)
BR (1)	BR9714086A (id)
CA (1)	CA2275634A1 (id)
CZ (1)	CZ229999A3 (id)
EA (1)	EA003995B1 (id)
HU (1)	HUP0000464A3 (id)
ID (1)	ID22807A (id)
IL (1)	IL130537A (id)
NZ (1)	NZ336420A (id)
PL (1)	PL334237A1 (id)
SK (1)	SK284351B6 (id)
TR (1)	TR199901471T2 (id)
UA (1)	UA67734C2 (id)
WO (1)	WO1998028279A1 (id)

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BRPI0718717A2 (pt)	2006-11-10	2013-11-26	Basf Se	Modificação cristalina ii de fipronil, fipronil sólido, processo para preparar a modificação cristalina ii, mistura pesticida ou parasiticida sinergística, composição pesticida ou parasiticida, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, métodos para controlar pragas, para proteger uma planta da infestação e ataque por pragas, para proteger semente, e para tratar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas, semente, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, e, processo para a preparação de uma composição para trtar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas
JP5931322B2 (ja)	2006-11-10	2016-06-08	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	フィプロニルの結晶変態
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EA200900654A1 (ru)	2006-11-30	2009-12-30	Басф Се	Агрохимические композиции, содержащие сополимеры 1-винил-2-пирролидинона
CA2668564A1 (en)	2006-11-30	2008-06-05	Basf Se	Agrochemical formulations comprising n-vinylamid co-polymers
EP2164323A1 (en)	2006-12-15	2010-03-24	Rohm and Haas Company	Mixtures comprising 1-methylcyclopropene
DE102006061538A1 (de)	2006-12-27	2008-07-03	Bayer Healthcare Ag	Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren
DE102006061537A1 (de)	2006-12-27	2008-07-03	Bayer Healthcare Ag	Mittel zur Bekämpfung von Parasiten an Tieren
AU2008206921B2 (en)	2007-01-19	2012-11-01	Basf Se	Fungicidal mixtures of 1-methylpyrazole-4-ylcarboxylic acid anilides and azolopyrimidinylamines
KR20090107070A (ko)	2007-01-26	2009-10-12	바스프 에스이	동물 해충 ⅱ의 퇴치를 위한 3-아미노-1,2-벤즈이소티아졸 화합물
EP1952690A3 (en)	2007-01-31	2009-04-22	Basf Se	Pesticidal mixtures based on triazolopyrimidines and insecticides
EP2679094A1 (en)	2007-02-06	2014-01-01	Basf Se	Pesticidal mixtures
CN104206402B (zh)	2007-04-12	2018-04-24	巴斯夫欧洲公司	包含氰基亚磺酰亚胺基化合物的农药混合物
CA2682294A1 (en)	2007-04-23	2008-10-30	Basf Se	Plant productivity enhancement by combining chemical agents with transgenic modifications
MX2010001666A (es)	2007-08-16	2010-03-10	Basf Se	Composiciones y metodos para el tratamiento de semillas.
NZ600929A (en)	2007-09-20	2014-02-28	Basf Se	Combinations comprising a fungicidal strain and an active compound
EP2500340A1 (en)	2008-01-25	2012-09-19	Syngenta Participations AG.	2-Cyanophenyl Sulfonamide Derivatives Useful as Pesticides
BRPI1005366B1 (pt)	2009-01-27	2022-02-08	Basf Se	Uso de um adesivo, formulação de revestimento de semente, kit de partes, método para regular o crescimento de plantas e/ou para controlar vegetação indesejada e método para controlar pestes
WO2010089244A1 (en)	2009-02-03	2010-08-12	Basf Se	Method for dressing seeds
WO2010100189A1 (en)	2009-03-04	2010-09-10	Basf Se	3-arylquinazolin-4-one compounds for combating invertebrate pests
WO2011003796A1 (en)	2009-07-06	2011-01-13	Basf Se	Pyridazine compounds for controlling invertebrate pests
EP2550264B1 (en)	2010-03-23	2016-06-08	Basf Se	Pyridazine compounds for controlling invertebrate pests
WO2013000572A1 (de)	2011-06-30	2013-01-03	2LUTION GmbH	Mittel zur bekämpfung von parasiten an tieren
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US6350771B1 (en) *	1996-12-24	2002-02-26	Rhone-Poulenc, Inc.	Pesticidal 1-arylpyrazoles

1997
- 1997-12-18 ID IDW990586A patent/ID22807A/id unknown
- 1997-12-18 UA UA99074126A patent/UA67734C2/uk unknown
- 1997-12-18 CA CA002275634A patent/CA2275634A1/en not_active Abandoned
- 1997-12-18 AU AU57598/98A patent/AU747450B2/en not_active Ceased
- 1997-12-18 HU HU0000464A patent/HUP0000464A3/hu unknown
- 1997-12-18 WO PCT/EP1997/007116 patent/WO1998028279A1/en not_active Ceased
- 1997-12-18 IL IL13053797A patent/IL130537A/en not_active IP Right Cessation
- 1997-12-18 TR TR1999/01471T patent/TR199901471T2/xx unknown
- 1997-12-18 PL PL97334237A patent/PL334237A1/xx unknown
- 1997-12-18 SK SK856-99A patent/SK284351B6/sk not_active IP Right Cessation
- 1997-12-18 CZ CZ992299A patent/CZ229999A3/cs unknown
- 1997-12-18 JP JP52835198A patent/JP2001506665A/ja active Pending
- 1997-12-18 BR BR9714086-4A patent/BR9714086A/pt unknown
- 1997-12-18 KR KR1019997005757A patent/KR20000062318A/ko not_active Abandoned
- 1997-12-18 AP APAP/P/1999/001586A patent/AP1004A/en active
- 1997-12-18 EP EP97953851A patent/EP0948487A1/en not_active Ceased
- 1997-12-18 EA EA199900598A patent/EA003995B1/ru not_active IP Right Cessation
- 1997-12-18 NZ NZ336420A patent/NZ336420A/en unknown
1999
- 1999-07-19 BG BG103592A patent/BG103592A/xx unknown

Also Published As

Publication number	Publication date
EA199900598A1 (ru)	2000-02-28
AP9901586A0 (en)	1999-06-30
PL334237A1 (en)	2000-02-14
EP0948487A1 (en)	1999-10-13
IL130537A0 (en)	2000-06-01
AU747450B2 (en)	2002-05-16
SK85699A3 (en)	2000-01-18
BG103592A (en)	2000-11-30
CZ229999A3 (cs)	1999-11-17
NZ336420A (en)	2001-04-27
HUP0000464A3 (en)	2002-01-28
KR20000062318A (ko)	2000-10-25
AU5759898A (en)	1998-07-17
AP1004A (en)	2001-08-28
WO1998028279A1 (en)	1998-07-02
BR9714086A (pt)	2000-05-09
IL130537A (en)	2004-08-31
TR199901471T2 (xx)	1999-10-21
JP2001506665A (ja)	2001-05-22
EA003995B1 (ru)	2003-12-25
ID22807A (id)	1999-12-09
HUP0000464A2 (hu)	2000-06-28
SK284351B6 (sk)	2005-02-04
CA2275634A1 (en)	1998-07-02

Publication	Publication Date	Title
UA67734C2 (uk)	2004-07-15	Похідні 1-арилпіразолу з пестицидними властивостями, пестицидна композиція, спосіб боротьби зі шкідниками та спосіб одержання похідних (варіанти)
KR0161284B1 (ko)	1998-12-01	3-시아노-5-알콕시-1-아릴피라졸류의 살충제
JP3986085B2 (ja)	2007-10-03	新規な５―アミノ―３―シアノ―４―エチルスルフィニル―１―フェニル―ピラゾール化合物及びその農薬としての使用
ES2297867T3 (es)	2008-05-01	1-aril-pirazoles pesticidas.
EA003186B1 (ru)	2003-02-27	Пестицидные 1-арилпиразолы
JPH03115266A (ja)	1991-05-16	Ｎ―フェニルピラゾール誘導体
WO2001000614A1 (en)	2001-01-04	Pyrazole derivatives and process for producing the same, and pesticides containing the same as the active ingredient
RU2077201C1 (ru)	1997-04-20	Производные 1-фенилимидазола, способ борьбы с вредителями сельского хозяйства и композиция для пестицидной обработки
KR100742976B1 (ko)	2007-07-26	살충용 1-아릴-3-이미노피라졸
JPH05148240A (ja)	1993-06-15	１−アリール−５−（置換アルキリデンイミノ）ピラゾール
ES2273820T3 (es)	2007-05-16	Pesticidas 3-tiometilpirazolico.
PT94386B (pt)	1996-12-31	Processo para a preparacao de derivados de n-fenilpirazol e de composicoes pesticidas que os contem
KR100602814B1 (ko)	2006-07-19	살충용 1-아릴피라졸
EA009644B1 (ru)	2008-02-28	Производные 1-арил-3-амидоксимпиразола, способы их получения, пестицидная композиция на их основе и их применение для борьбы с вредителями
RU2063688C1 (ru)	1996-07-20	Производные пирролов, инсектоакарицидная композиция и способ борьбы с насекомыми и клещами
JP2000256111A (ja)	2000-09-19	セスキテルペンピリジンアルカロイド化合物を含有する農園芸用殺虫剤
MXPA99005963A (en)	2000-01-01	Pesticidal 1-aryl and pyridylpyrazole derivatives