IL130537A - 1 - Arylpirazoles, pesticide preparations containing them, process for their preparation and methods for pest control - Google Patents

1 - Arylpirazoles, pesticide preparations containing them, process for their preparation and methods for pest control

Info

Publication number: IL130537A
Authority: IL; Israel
Prior art keywords: alkyl; formula; compound; amino; halogen
Prior art date: 1996-12-24

Application number

IL13053797A

Other languages

English (en)

Hebrew (he)

Other versions

IL130537A0 (en

Original Assignee

Bayer Cropscience Sa

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

2004-08-31

1997-12-18 Application filed by Bayer Cropscience Sa filed Critical Bayer Cropscience Sa

2000-06-01 Publication of IL130537A0 publication Critical patent/IL130537A0/xx

2004-08-31 Publication of IL130537A publication Critical patent/IL130537A/en

Links

239000000203 mixture Substances 0.000 title claims description 87
241000607479 Yersinia pestis Species 0.000 title claims description 38
238000000034 method Methods 0.000 title claims description 36
230000000361 pesticidal effect Effects 0.000 title claims description 7
125000004961 1-arylpyrazolyl group Chemical group 0.000 title claims description 4
230000008569 process Effects 0.000 title description 5
238000002360 preparation method Methods 0.000 title description 3
-1 1H-pyrazol-1-yl Chemical group 0.000 claims abstract description 105
125000000217 alkyl group Chemical group 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 42
229910052736 halogen Inorganic materials 0.000 claims abstract description 28
150000002367 halogens Chemical class 0.000 claims abstract description 28
125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
150000003254 radicals Chemical class 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 8
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims abstract description 6
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
125000006519 CCH3 Chemical group 0.000 claims abstract description 4
125000003435 aroyl group Chemical group 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000004429 atom Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000001475 halogen functional group Chemical group 0.000 claims abstract description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 3
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 3
102220315634 rs1196125127 Human genes 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 146
241001465754 Metazoa Species 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 24
241000238631 Hexapoda Species 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
230000037396 body weight Effects 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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 2
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 description 2
150000001879 copper Chemical class 0.000 claims description 2
238000007033 dehydrochlorination reaction Methods 0.000 claims description 2
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
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 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
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
241000238421 Arthropoda Species 0.000 description 32
239000004480 active ingredient Substances 0.000 description 32
241000196324 Embryophyta Species 0.000 description 31
239000000243 solution Substances 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
239000008187 granular material Substances 0.000 description 17
239000007788 liquid Substances 0.000 description 17
239000000843 powder Substances 0.000 description 17
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239000002689 soil Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
238000011282 treatment Methods 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000004615 ingredient Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
238000009472 formulation Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
238000005507 spraying Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
241001124076 Aphididae Species 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000010992 reflux Methods 0.000 description 9
241000254173 Coleoptera Species 0.000 description 8
206010061217 Infestation Diseases 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
230000009885 systemic effect Effects 0.000 description 8
QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
241000255925 Diptera Species 0.000 description 7
108010034145 Helminth Proteins Proteins 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
244000144972 livestock Species 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
241000256602 Isoptera Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
241000251539 Vertebrata <Metazoa> Species 0.000 description 6
240000008042 Zea mays Species 0.000 description 6
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239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000012360 testing method Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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241000258937 Hemiptera Species 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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239000000654 additive Substances 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
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239000000543 intermediate Substances 0.000 description 5
230000002262 irrigation Effects 0.000 description 5
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000000725 suspension Substances 0.000 description 5
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241001600408 Aphis gossypii Species 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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239000002585 base Substances 0.000 description 4
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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239000011148 porous material Substances 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
244000000040 protozoan parasite Species 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-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
238000001228 spectrum Methods 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
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
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
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
150000003573 thiols Chemical class 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
239000013598 vector Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—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)

IL13053797A 1996-12-24 1997-12-18 1 - Arylpirazoles, pesticide preparations containing them, process for their preparation and methods for pest control IL130537A (en)

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 (2)

Publication Number	Publication Date
IL130537A0 IL130537A0 (en)	2000-06-01
IL130537A true IL130537A (en)	2004-08-31

Family

ID=21873029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13053797A IL130537A (en)	1996-12-24	1997-12-18	1 - Arylpirazoles, pesticide preparations containing them, process for their preparation and methods for pest control

Country Status (19)

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

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US6350771B1 (en) *	1996-12-24	2002-02-26	Rhone-Poulenc, Inc.	Pesticidal 1-arylpyrazoles
DE19824487A1 (de)	1998-06-02	1999-12-09	Bayer Ag	Substituierte 3-Thiocarbamoylpyrazole
DE19853560A1 (de) *	1998-11-20	2000-05-25	Bayer Ag	Verfahren zur Herstellung von 5-Amino-3-(thio)carbamoylpyrazolen
US6531501B1 (en)	1998-12-11	2003-03-11	Aventis Cropscience, S.A.	Control of arthropods in animals
AR021608A1 (es) *	1998-12-11	2002-07-31	Merial Ltd	Represion de artropodos en animales
ES2409630T3 (es)	1999-12-02	2013-06-27	Merial Limited	Control de artrópodos en animales
FR2805971B1 (fr)	2000-03-08	2004-01-30	Aventis Cropscience Sa	Procedes de traitement et/ou de protection des cultures contre les arthropodes et compositions utiles pour de tels procedes
ZA200601794B (en) *	2003-09-04	2007-04-25	Bayer Cropscience Sa	Pesticidal 5-substituted-oxyalkylamino-1-arylpyrazole derivatives
EP1727805B1 (en)	2004-03-15	2008-07-02	Merial Limited	1-phenyl and 1-pyridylpyrazole derivatives and their use as pesticides
US20050234119A1 (en) *	2004-04-16	2005-10-20	Soll Mark D	Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals
WO2007147888A1 (en)	2006-06-22	2007-12-27	Basf Se	Malononitrile compounds
PT2514316E (pt)	2006-09-14	2014-03-06	Basf Se	Composição de pesticida
NZ576524A (en)	2006-11-10	2012-01-12	Basf Se	Crystalline modification of fipronil
MX2009004323A (es)	2006-11-10	2009-05-05	Basf Se	Nueva modificacion cristalina.
AU2007316640B2 (en)	2006-11-10	2012-11-29	Basf Se	Crystalline modification of fipronil
UA110598C2 (uk)	2006-11-10	2016-01-25	Басф Се	Спосіб одержання кристалічної модифікації фіпронілу
PL2088856T3 (pl)	2006-11-30	2011-02-28	Basf Se	Preparaty agrochemiczne zawierające kopolimery oparte na diizocyjanianach
JP5323715B2 (ja)	2006-11-30	2013-10-23	ビーエーエスエフソシエタス・ヨーロピア	１−ビニル−２−ピロリジノンコポリマーを含む農薬製剤
PL2099292T3 (pl)	2006-11-30	2010-10-29	Basf Se	Preparaty agrochemiczne zawierające kopolimery N-winyloamidu
EP2258177A3 (en)	2006-12-15	2011-11-09	Rohm and Haas Company	Mixtures comprising 1-methylcyclopropene
DE102006061537A1 (de)	2006-12-27	2008-07-03	Bayer Healthcare Ag	Mittel zur Bekämpfung von Parasiten an Tieren
DE102006061538A1 (de)	2006-12-27	2008-07-03	Bayer Healthcare Ag	Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren
US8211828B2 (en)	2007-01-19	2012-07-03	Basf Se	Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxanilides and azolopyrimidinylamines
ATE549325T1 (de)	2007-01-26	2012-03-15	Basf Se	3-amino-1,2-benzisothiazol-verbindungen zur bekämpfung von tierpest ii
EP1952690A3 (en)	2007-01-31	2009-04-22	Basf Se	Pesticidal mixtures based on triazolopyrimidines and insecticides
EP2109366A2 (en)	2007-02-06	2009-10-21	Basf Se	Pesticidal mixtures
CN108402068B (zh)	2007-04-12	2021-12-03	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
US20100093715A1 (en)	2007-04-23	2010-04-15	Basf Se	Plant productivity enhancement by combining chemical agents with transgenic modifications
NZ599997A (en)	2007-08-16	2013-08-30	Basf Se	Seed treatment compositions and methods
EA020203B1 (ru)	2007-09-20	2014-09-30	Басф Се	Композиции и агенты, содержащие фунгицидный штамм и активное соединение
US20100311582A1 (en)	2008-01-25	2010-12-09	Syngenta Crop Protection, Inc.	Chemical compounds
ES2524819T3 (es)	2009-01-27	2014-12-12	Basf Se	Procedimiento de tratamiento de semillas
WO2010089244A1 (en)	2009-02-03	2010-08-12	Basf Se	Method for dressing seeds
AR075717A1 (es)	2009-03-04	2011-04-20	Basf Se	Compuestos de 3- aril quinazolin -4- ona para combatir plagas de invertebrados
EP2451804B1 (en)	2009-07-06	2014-04-30	Basf Se	Pyridazine compounds for controlling invertebrate pests
WO2011117286A1 (en)	2010-03-23	2011-09-29	Basf Se	Pyridazine compounds for controlling invertebrate pests
EP2725899B1 (de)	2011-06-30	2016-09-28	Hansen-AB GmbH	Mittel zur bekämpfung von parasiten an tieren
JO3626B1 (ar)	2012-02-23	2020-08-27	Merial Inc	تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
AR100304A1 (es)	2014-02-05	2016-09-28	Basf Corp	Formulación de recubrimiento de semillas
WO2025242701A1 (en)	2024-05-22	2025-11-27	Basf Se	Seed treatment compositions

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US5232940A (en) *	1985-12-20	1993-08-03	Hatton Leslie R	Derivatives of N-phenylpyrazoles
GB8713768D0 (en) *	1987-06-12	1987-07-15	May & Baker Ltd	Compositions of matter
NO179282C (no) *	1991-01-18	1996-09-11	Rhone Poulenc Agrochimie	Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter
AU1191292A (en) *	1991-02-11	1992-09-07	Schering Agrochemicals Limited	Imidazole pesticides
GB9120641D0 (en) *	1991-09-27	1991-11-06	Ici Plc	Heterocyclic compounds
GB9306184D0 (en) *	1993-03-25	1993-05-19	Zeneca Ltd	Heteroaromatic compounds
DE4343832A1 (de) *	1993-12-22	1995-06-29	Bayer Ag	Substituierte 1-Arylpyrazole
DE19511269A1 (de) *	1994-03-30	1995-10-05	Ciba Geigy Ag	Pyrazole
DE4414333A1 (de) *	1994-04-25	1995-10-26	Bayer Ag	Substituierte Pyridylpyrazole
US6350771B1 (en) *	1996-12-24	2002-02-26	Rhone-Poulenc, Inc.	Pesticidal 1-arylpyrazoles

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

Also Published As

Publication number	Publication date
SK284351B6 (sk)	2005-02-04
BG103592A (en)	2000-11-30
AP1004A (en)	2001-08-28
CA2275634A1 (en)	1998-07-02
IL130537A0 (en)	2000-06-01
PL334237A1 (en)	2000-02-14
SK85699A3 (en)	2000-01-18
TR199901471T2 (xx)	1999-10-21
UA67734C2 (uk)	2004-07-15
AU747450B2 (en)	2002-05-16
KR20000062318A (ko)	2000-10-25
WO1998028279A1 (en)	1998-07-02
JP2001506665A (ja)	2001-05-22
HUP0000464A3 (en)	2002-01-28
EA199900598A1 (ru)	2000-02-28
AP9901586A0 (en)	1999-06-30
ID22807A (id)	1999-12-09
HUP0000464A2 (hu)	2000-06-28
AU5759898A (en)	1998-07-17
BR9714086A (pt)	2000-05-09
EA003995B1 (ru)	2003-12-25
CZ229999A3 (cs)	1999-11-17
NZ336420A (en)	2001-04-27
EP0948487A1 (en)	1999-10-13

Legal Events

Date	Code	Title	Description
2005-01-24	FF	Patent granted
2006-01-15	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AP1004A (en)	2001-08-28	Pesticidal 1-aryl and pyridylpyrazole derivatives.
US6350771B1 (en)	2002-02-26	Pesticidal 1-arylpyrazoles
CA2275635C (en)	2008-11-25	Pesticidal 1-arylpyrazoles
CA2283465C (en)	2008-06-03	Pesticidal 1-aryl-3-iminopyrazoles
EP0973747B1 (en)	2003-10-15	Pesticidal 1-arylpyrazoles
US6500850B2 (en)	2002-12-31	Pesticidal 1-arylpyrazoles
US6008353A (en)	1999-12-28	Pesticidal 1-arylpyrazole boranes
US20020016468A1 (en)	2002-02-07	Pesticidal 1-arylpyrazole derivatives
MXPA99005963A (en)	2000-01-01	Pesticidal 1-aryl and pyridylpyrazole derivatives