IL109791A - 13-alkyl-23-imino derivatives of ll-f28249 compounds and their use as endo and ecto-parasticidal insecticidal acaricidal and nematocidal agents - Google Patents

13-alkyl-23-imino derivatives of ll-f28249 compounds and their use as endo and ecto-parasticidal insecticidal acaricidal and nematocidal agents

Info

Publication number: IL109791A
Authority: IL; Israel
Prior art keywords: compounds; compound; test; mixture; alkyl
Prior art date: 1989-09-11

Application number

IL10979190A

Other languages

English (en)

Inventor

Brian Lee Buckwalter

Shin-Shyong Tseng

Timothy Claude Barden

Original Assignee

American Cyanamid Co

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.)

1989-09-11

Filing date

1990-08-06

Publication date

1996-06-18

1989-09-11 Priority claimed from US07/405,808 external-priority patent/US5030650A/en

1989-12-22 Priority claimed from US07/455,686 external-priority patent/US5055486A/en

1990-08-06 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1996-06-18 Publication of IL109791A publication Critical patent/IL109791A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 119
230000000895 acaricidal effect Effects 0.000 title description 10
230000000749 insecticidal effect Effects 0.000 title description 9
239000005645 nematicide Substances 0.000 title description 2
241000244206 Nematoda Species 0.000 claims abstract description 7
244000078703 ectoparasite Species 0.000 claims abstract description 5
241001465754 Metazoa Species 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
206010061217 Infestation Diseases 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
241000238631 Hexapoda Species 0.000 abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
238000012360 testing method Methods 0.000 description 60
239000000203 mixture Substances 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
241000238876 Acari Species 0.000 description 37
239000000123 paper Substances 0.000 description 27
238000002360 preparation method Methods 0.000 description 27
238000011282 treatment Methods 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000000243 solution Substances 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
238000004458 analytical method Methods 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
229940073584 methylene chloride Drugs 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 22
230000003595 spectral effect Effects 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 21
241000196324 Embryophyta Species 0.000 description 20
239000000047 product Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000011156 evaluation Methods 0.000 description 18
239000012267 brine Substances 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
239000012085 test solution Substances 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
-1 c1~c4 allcoxy Chemical group 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 14
235000013601 eggs Nutrition 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
239000000843 powder Substances 0.000 description 12
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
241000257159 Musca domestica Species 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
239000006260 foam Substances 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000010586 diagram Methods 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000004033 plastic Substances 0.000 description 7
229920003023 plastic Polymers 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
241000699694 Gerbillinae Species 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 6
241000607479 Yersinia pestis Species 0.000 description 6
238000013019 agitation Methods 0.000 description 6
230000002141 anti-parasite Effects 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
238000009472 formulation Methods 0.000 description 6
150000002431 hydrogen Chemical group 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000007921 spray Substances 0.000 description 6
239000012258 stirred mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
241001124076 Aphididae Species 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241001425390 Aphis fabae Species 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
244000045232 Canavalia ensiformis Species 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
235000002637 Nicotiana tabacum Nutrition 0.000 description 4
206010039509 Scab Diseases 0.000 description 4
241000208241 Tropaeolum Species 0.000 description 4
230000009418 agronomic effect Effects 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
230000009969 flowable effect Effects 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
230000001069 nematicidal effect Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
238000012546 transfer Methods 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
241000256244 Heliothis virescens Species 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
241001494479 Pecora Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
WFAULHLDTDDABL-UHFFFAOYSA-N Proxazole citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(CC)C1=NOC(CCN(CC)CC)=N1 WFAULHLDTDDABL-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000004849 alkoxymethyl group Chemical group 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000009395 breeding Methods 0.000 description 3
230000001488 breeding effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
235000013305 food Nutrition 0.000 description 3
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
239000004530 micro-emulsion Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
241000239290 Araneae Species 0.000 description 2
241001414720 Cicadellidae Species 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
XKTIELJOWPDXMX-UHFFFAOYSA-N N[S](N)(F)(F)F Chemical compound N[S](N)(F)(F)F XKTIELJOWPDXMX-UHFFFAOYSA-N 0.000 description 2
241000208125 Nicotiana Species 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
235000010617 Phaseolus lunatus Nutrition 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000243796 Trichostrongylus colubriformis Species 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000003096 antiparasitic agent Substances 0.000 description 2
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239000000969 carrier Substances 0.000 description 2
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230000001984 ectoparasiticidal effect Effects 0.000 description 2
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000007306 functionalization reaction Methods 0.000 description 2
238000003304 gavage Methods 0.000 description 2
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230000002140 halogenating effect Effects 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
244000000013 helminth Species 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
230000001524 infective effect Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
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SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 2
YNFMRVVYUVPIAN-AQUURSMBSA-N nemadectin Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C(C)C)O[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 YNFMRVVYUVPIAN-AQUURSMBSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
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HBJHXACNQULZAH-FBMGVBCBSA-N 1-amino-2-[(e)-2-hexyldodec-2-enyl]guanidine Chemical compound CCCCCCCCC\C=C(CN=C(N)NN)/CCCCCC HBJHXACNQULZAH-FBMGVBCBSA-N 0.000 description 1
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000002323 endectocidal effect Effects 0.000 description 1
244000079386 endoparasite Species 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
YNFMRVVYUVPIAN-UHFFFAOYSA-N nemadectin alpha Natural products C1C(O)C(C)C(C(C)=CC(C)C)OC11OC(CC=C(C)CC(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 YNFMRVVYUVPIAN-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000019617 pupation Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Pest Control & Pesticides (AREA)
Genetics & Genomics (AREA)
Tropical Medicine & Parasitology (AREA)
Biotechnology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Agronomy & Crop Science (AREA)
Molecular Biology (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL10979190A 1989-09-11 1990-08-06 13-alkyl-23-imino derivatives of ll-f28249 compounds and their use as endo and ecto-parasticidal insecticidal acaricidal and nematocidal agents IL109791A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/405,808 US5030650A (en)	1989-09-11	1989-09-11	13-halo-23-imino derivatives of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
US07/455,686 US5055486A (en)	1989-12-22	1989-12-22	13-alkyl-23-imino derivative of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
IL9530490A IL95304A (en)	1989-09-11	1990-08-06	13-halo-23-imino derivatives of ll-f28249 compounds and their use as endo- and ecto-parasiticidal insecticidal acaricidal and nematocidal agents

Publications (1)

Publication Number	Publication Date
IL109791A true IL109791A (en)	1996-06-18

Family

ID=27019245

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10979190A IL109791A (en)	1989-09-11	1990-08-06	13-alkyl-23-imino derivatives of ll-f28249 compounds and their use as endo and ecto-parasticidal insecticidal acaricidal and nematocidal agents

Country Status (21)

Country	Link
EP (1)	EP0423445B1 (de)
JP (1)	JP3026827B2 (de)
KR (2)	KR0160972B1 (de)
CN (2)	CN1032004C (de)
AT (1)	ATE130006T1 (de)
AU (1)	AU631454B2 (de)
BG (1)	BG60271B1 (de)
BR (1)	BR9004494A (de)
DE (1)	DE69023454T2 (de)
DK (1)	DK0423445T3 (de)
ES (1)	ES2081880T3 (de)
GR (1)	GR3018033T3 (de)
HU (1)	HU217357B (de)
IE (1)	IE71210B1 (de)
IL (1)	IL109791A (de)
PL (1)	PL164168B1 (de)
PT (1)	PT95241B (de)
RU (1)	RU2070885C1 (de)
SI (1)	SI9011710B (de)
UA (1)	UA41246C2 (de)
YU (1)	YU47592B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4988824A (en) *	1989-09-11	1991-01-29	Maulding Donald R	Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds
US5229416A (en) *	1992-04-29	1993-07-20	Merck & Co., Inc.	Avermectin difluoro derivatives
DE19654079A1 (de)	1996-12-23	1998-06-25	Bayer Ag	Endo-ekto-parasitizide Mittel
DE102004053964A1 (de)	2004-11-09	2006-05-11	Bayer Healthcare Ag	Mittel gegen Demodikose
CN106831811B (zh) *	2015-08-12	2018-10-26	内蒙古佳瑞米精细化工有限公司	一种制备高含量尼莫克汀的方法
US20210137960A1 (en)	2018-02-01	2021-05-13	Yale University	Compositions and methods for inhibition of nuclear-penetrating antibodies

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ221077A (en) *	1986-07-18	1990-06-26	Ciba Geigy Ag	13b-alkyl milbemycins and use as parasiticides
DE3750355T2 (de) *	1986-09-12	1995-04-06	American Cyanamid Co	23-Oxo(keto) und 23-Imino-Derivate von LL-F28249-Verbindungen.
US4831016A (en) *	1986-10-31	1989-05-16	Merck & Co., Inc.	Reduced avermectin derivatives
US4886829A (en) *	1987-03-06	1989-12-12	American Cyanamid Company	23-Oxo (keto) and 23-imino derivatives of mono- and diepoxy LL-F28249 compounds
US4806527A (en) *	1987-03-16	1989-02-21	Merck & Co., Inc.	Avermectin derivatives
US5830875A (en) *	1989-10-30	1998-11-03	Merck & Co., Inc.	24-and 25-substituted avermectin and milbemycin derivatives

1990
- 1990-08-03 AT AT90114920T patent/ATE130006T1/de not_active IP Right Cessation
- 1990-08-03 DE DE69023454T patent/DE69023454T2/de not_active Expired - Lifetime
- 1990-08-03 EP EP90114920A patent/EP0423445B1/de not_active Expired - Lifetime
- 1990-08-03 ES ES90114920T patent/ES2081880T3/es not_active Expired - Lifetime
- 1990-08-03 DK DK90114920.3T patent/DK0423445T3/da active
- 1990-08-06 IL IL10979190A patent/IL109791A/en not_active IP Right Cessation
- 1990-08-30 CN CN90107011A patent/CN1032004C/zh not_active Expired - Fee Related
- 1990-09-07 PT PT95241A patent/PT95241B/pt not_active IP Right Cessation
- 1990-09-07 JP JP2235957A patent/JP3026827B2/ja not_active Expired - Lifetime
- 1990-09-10 BG BG092811A patent/BG60271B1/bg unknown
- 1990-09-10 YU YU171090A patent/YU47592B/sh unknown
- 1990-09-10 BR BR909004494A patent/BR9004494A/pt not_active IP Right Cessation
- 1990-09-10 SI SI9011710A patent/SI9011710B/sl not_active IP Right Cessation
- 1990-09-10 UA UA4831124A patent/UA41246C2/uk unknown
- 1990-09-10 HU HU844/90A patent/HU217357B/hu not_active IP Right Cessation
- 1990-09-10 IE IE327490A patent/IE71210B1/en not_active IP Right Cessation
- 1990-09-10 KR KR1019900014282A patent/KR0160972B1/ko not_active Expired - Fee Related
- 1990-09-10 AU AU62357/90A patent/AU631454B2/en not_active Expired
- 1990-09-10 PL PL90286823A patent/PL164168B1/pl unknown
- 1990-09-10 RU SU904831124A patent/RU2070885C1/ru not_active IP Right Cessation
1994
- 1994-11-24 CN CN94118512A patent/CN1053556C/zh not_active Expired - Fee Related
1995
- 1995-11-09 GR GR940403514T patent/GR3018033T3/el unknown
1998
- 1998-06-23 KR KR1019980023560A patent/KR0168751B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
YU171090A (sh)	1992-12-21
JPH03106886A (ja)	1991-05-07
AU6235790A (en)	1991-03-14
CN1032004C (zh)	1996-06-12
KR0168751B1 (ko)	1999-01-15
EP0423445A1 (de)	1991-04-24
UA41246C2 (uk)	2001-09-17
PL286823A1 (en)	1991-10-07
ES2081880T3 (es)	1996-03-16
IE71210B1 (en)	1997-02-12
HUT54691A (en)	1991-03-28
YU47592B (sh)	1995-10-24
CN1115600A (zh)	1996-01-31
RU2070885C1 (ru)	1996-12-27
ATE130006T1 (de)	1995-11-15
JP3026827B2 (ja)	2000-03-27
BG60271B2 (bg)	1994-03-31
CN1053556C (zh)	2000-06-21
DE69023454D1 (de)	1995-12-14
HU217357B (hu)	2000-01-28
KR910006491A (ko)	1991-04-29
EP0423445B1 (de)	1995-11-08
SI9011710A (sl)	1998-02-28
GR3018033T3 (en)	1996-02-29
BR9004494A (pt)	1991-09-10
CN1050193A (zh)	1991-03-27
AU631454B2 (en)	1992-11-26
DK0423445T3 (da)	1995-12-11
PT95241A (pt)	1991-06-25
PL164168B1 (pl)	1994-06-30
SI9011710B (sl)	2000-12-31
KR0160972B1 (ko)	1998-12-01
PT95241B (pt)	1997-06-30
DE69023454T2 (de)	1996-06-05
IE903274A1 (en)	1991-03-27
BG60271B1 (bg)	1994-03-31

Legal Events

Date	Code	Title
1996-11-14	FF	Patent granted
1997-03-18	KB	Patent renewed
1997-04-15	KB	Patent renewed
2000-12-06	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0298196B1 (de)	1993-06-02	Imidazol-Verbindung und diese enthaltende biozide Zusammensetzungen
HK1005448B (en)	1999-01-08	Imidazole compounds and blocidal compositions comprising the same
EP0434940A2 (de)	1991-07-03	N-oxygenierte Arylpyrrole als insektizide, akarizide und nematizide Wirkstoffe
US5130328A (en)	1992-07-14	N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents
US5030650A (en)	1991-07-09	13-halo-23-imino derivatives of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
EP0423445B1 (de)	1995-11-08	13-Alkyl-23-Imino und 13-Halo-23-Imino-Derivate von LL-F28249-Verbindungen und ihre Verwendung als Endo- und Ectoparasitizide, Insektizide, Akarizide und Nematozide Mittel
NZ241095A (en)	1994-07-26	2-phenyl-substituted pyrroline derivatives and pesticidal compositions
DK168159B1 (da)	1994-02-21	Fremgangsmåde til fremstilling af med avermectiner og milbemyciner beslægtede forbindelser
JP3242943B2 (ja)	2001-12-25	殺昆虫剤、殺ダニ剤、殺線虫剤および殺軟体動物剤として有用な新規なｎ−アシル化されたアリールピロール類
US4400517A (en)	1983-08-23	Phosphoric esters derived from 1,2,4-triazole having an insecticidal, nematocidal and acaricidal action, and their preparation
JP2553156B2 (ja)	1996-11-13	アリールピロール殺昆虫、殺ダニおよび殺線虫剤およびそれらの調製方法
EP0709372B1 (de)	1998-08-26	N-Arylthiohydrazon-Derivate als insektizide und akarazide Mittel
AU657214B2 (en)	1995-03-02	New derivatives of 7-ethynyl alpha-(methoxymethylene) 1-naphthalene acetic acid, their preparation process and their use as pesticides
CN110066270B (zh)	2021-02-26	多酰胺类化合物及其制备方法与应用
US5055486A (en)	1991-10-08	13-alkyl-23-imino derivative of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
RU2120943C1 (ru)	1998-10-27	Производные дорамектина, способы их получения, способы лечения
US4689342A (en)	1987-08-25	Certain insecticidal cyclopropane carboxylic acid derivatives
EP1004241A1 (de)	2000-05-31	2-Aryl-Delta 2-1,3,4-(oxa oder thia)Diazoline enthaltende Insektizide und akarizide Mittel
GB1567481A (en)	1980-05-14	Benzodithiole derivatives
GB2093841A (en)	1982-09-08	Esters of heterocyclic alcohols having pesticidal activity
US3629430A (en)	1971-12-21	Isoxazole fungicidal compositions and methods of use
US6242647B1 (en)	2001-06-05	Insecticidal biphenylthiohydrazides
EP0031699A1 (de)	1981-07-08	Benzimidazolin-Salze, ihre Herstellung und sie enthaltende Zusammensetzungen
US4024252A (en)	1977-05-17	2-(5-Ethyl-6-bromothiazolo[3,2-b]-5-triazolyl)thiophosphonate esters, compositions and method of use
US4358607A (en)	1982-11-09	Chloro-substituted benzospiro cyclopropane carboxylic acid