IL130537A

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

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

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
241000238876 Acari Species 0.000 description 16
244000000013 helminth Species 0.000 description 16
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241000244206 Nematoda Species 0.000 description 15
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
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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
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
241000258937 Hemiptera Species 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
239000000654 additive Substances 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
239000004562 water dispersible granule Substances 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
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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239000003086 colorant Substances 0.000 description 4
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239000002270 dispersing agent Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
230000000749 insecticidal effect Effects 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
229910002012 Aerosil® Inorganic materials 0.000 description 3
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
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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 3
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OYFNHRSGJVXFON-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(SC)=C(N)N1C1=CC=C(C(F)(F)F)C=C1Cl OYFNHRSGJVXFON-UHFFFAOYSA-N 0.000 description 2
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244000000040 protozoan parasite Species 0.000 description 1
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125000004076 pyridyl group Chemical group 0.000 description 1
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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
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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
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230000003612 virological effect Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
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238000009736 wetting Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
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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