AP76A - Porphyric Insecticides - Google Patents

Porphyric Insecticides Download PDF

Info

Publication number: AP76A
Authority: AP; ARIPO
Prior art keywords: delta; aminolevulinic acid; ala; composition; tetrapyrroles
Prior art date: 1988-01-13

Application number

APAP/P/1989/000112A

Other languages

English (en)

Inventor

John A Juvik

Constantin A Rebeiz

Carole C Rebeiz

Original Assignee

Univ Illinois

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.)

1988-01-13

Filing date

1989-01-13

Publication date

1990-03-07

1989-01-13 Application filed by Univ Illinois filed Critical Univ Illinois

1990-03-07 Application granted granted Critical

1990-03-07 Publication of AP76A publication Critical patent/AP76A/en

Links

239000002917 insecticide Substances 0.000 title claims description 16
239000000203 mixture Substances 0.000 claims abstract description 58
230000000749 insecticidal effect Effects 0.000 claims abstract description 21
241000238631 Hexapoda Species 0.000 claims description 63
238000009825 accumulation Methods 0.000 claims description 54
ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 42
239000003623 enhancer Substances 0.000 claims description 37
239000000411 inducer Substances 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 10
229960002749 aminolevulinic acid Drugs 0.000 claims description 7
239000004009 herbicide Substances 0.000 claims description 7
230000002363 herbicidal effect Effects 0.000 claims description 6
230000001939 inductive effect Effects 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 4
239000002518 antifoaming agent Substances 0.000 claims description 4
239000002270 dispersing agent Substances 0.000 claims description 4
239000002895 emetic Substances 0.000 claims description 4
239000003995 emulsifying agent Substances 0.000 claims description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
239000000080 wetting agent Substances 0.000 claims description 4
230000034994 death Effects 0.000 description 85
230000001418 larval effect Effects 0.000 description 82
235000005911 diet Nutrition 0.000 description 48
230000037213 diet Effects 0.000 description 47
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 43
238000011282 treatment Methods 0.000 description 37
239000000049 pigment Substances 0.000 description 27
239000007921 spray Substances 0.000 description 23
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 16
241000219823 Medicago Species 0.000 description 15
230000001419 dependent effect Effects 0.000 description 14
230000000694 effects Effects 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
238000011534 incubation Methods 0.000 description 13
235000012054 meals Nutrition 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 12
239000013256 coordination polymer Substances 0.000 description 12
238000002474 experimental method Methods 0.000 description 12
229950003776 protoporphyrin Drugs 0.000 description 11
239000000126 substance Substances 0.000 description 11
210000001519 tissue Anatomy 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000006378 damage Effects 0.000 description 9
230000005284 excitation Effects 0.000 description 9
210000000087 hemolymph Anatomy 0.000 description 9
102000004169 proteins and genes Human genes 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
241000255967 Helicoverpa zea Species 0.000 description 8
230000008859 change Effects 0.000 description 8
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 8
229920000053 polysorbate 80 Polymers 0.000 description 8
210000003491 skin Anatomy 0.000 description 7
-1 uroporphyrin octamethyl ester Chemical class 0.000 description 7
230000037396 body weight Effects 0.000 description 6
230000007246 mechanism Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
241000894007 species Species 0.000 description 6
230000005945 translocation Effects 0.000 description 6
108010052832 Cytochromes Proteins 0.000 description 5
102000018832 Cytochromes Human genes 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 5
230000002708 enhancing effect Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
239000012528 membrane Substances 0.000 description 5
230000037361 pathway Effects 0.000 description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
102000004895 Lipoproteins Human genes 0.000 description 4
108090001030 Lipoproteins Proteins 0.000 description 4
230000006696 biosynthetic metabolic pathway Effects 0.000 description 4
238000011161 development Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
235000013305 food Nutrition 0.000 description 4
239000011521 glass Substances 0.000 description 4
150000003278 haem Chemical class 0.000 description 4
238000005286 illumination Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000001814 pectin Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
238000005507 spraying Methods 0.000 description 4
230000002195 synergetic effect Effects 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
QSHWIQZFGQKFMA-UHFFFAOYSA-N Porphobilinogen Natural products NCC=1NC=C(CCC(O)=O)C=1CC(O)=O QSHWIQZFGQKFMA-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229930002875 chlorophyll Natural products 0.000 description 3
235000019804 chlorophyll Nutrition 0.000 description 3
ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
238000000605 extraction Methods 0.000 description 3
231100000518 lethal Toxicity 0.000 description 3
230000001665 lethal effect Effects 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
UHSGPDMIQQYNAX-UHFFFAOYSA-N protoporphyrinogen Chemical compound C1C(=C(C=2C=C)C)NC=2CC(=C(C=2CCC(O)=O)C)NC=2CC(N2)=C(CCC(O)=O)C(C)=C2CC2=C(C)C(C=C)=C1N2 UHSGPDMIQQYNAX-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
239000011701 zinc Substances 0.000 description 3
208000031648 Body Weight Changes Diseases 0.000 description 2
102000000634 Cytochrome c oxidase subunit IV Human genes 0.000 description 2
108090000365 Cytochrome-c oxidases Proteins 0.000 description 2
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
102000003875 Ferrochelatase Human genes 0.000 description 2
108010057394 Ferrochelatase Proteins 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000255993 Trichoplusia ni Species 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000004579 body weight change Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
ANWUQYTXRXCEMZ-NYABAGMLSA-L chlorophyllide a Chemical group C1([C@H](C2=O)C(=O)OC)=C(N3[Mg]N45)C2=C(C)\C3=C\C(=N2)C(CC)=C(C)\C2=C\C4=C(C=C)C(C)=C5\C=C/2[C@@H](C)[C@H](CCC(O)=O)C1=N\2 ANWUQYTXRXCEMZ-NYABAGMLSA-L 0.000 description 2
FQIVLXIUJLOKPL-DWZMLRRXSA-N coprogen Chemical compound C1CCN(O2)C(=O)\C=C(C)\CCOC(=O)[C@@H](NC(=O)C)CCCN(C(=O)\C=C(/C)CCO)O[Fe]2ON(C(=O)\C=C(/C)CCO)CCC[C@H]2C(=O)N[C@@H]1C(=O)N2 FQIVLXIUJLOKPL-DWZMLRRXSA-N 0.000 description 2
NIUVHXTXUXOFEB-UHFFFAOYSA-N coproporphyrinogen III Chemical compound C1C(=C(C=2C)CCC(O)=O)NC=2CC(=C(C=2C)CCC(O)=O)NC=2CC(N2)=C(CCC(O)=O)C(C)=C2CC2=C(C)C(CCC(O)=O)=C1N2 NIUVHXTXUXOFEB-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000001066 destructive effect Effects 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000000695 excitation spectrum Methods 0.000 description 2
230000005281 excited state Effects 0.000 description 2
230000005283 ground state Effects 0.000 description 2
150000002432 hydroperoxides Chemical class 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
150000002678 macrocyclic compounds Chemical class 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
230000035772 mutation Effects 0.000 description 2
238000010606 normalization Methods 0.000 description 2
230000009013 pigment accumulation Effects 0.000 description 2
YPHQRHBJEUDWJW-UHFFFAOYSA-N porphobilinogen Chemical compound NCC1=NC=C(CCC(O)=O)[C]1CC(O)=O YPHQRHBJEUDWJW-UHFFFAOYSA-N 0.000 description 2
150000004032 porphyrins Chemical class 0.000 description 2
239000002243 precursor Substances 0.000 description 2
DASFNRASQHZIIW-XOTKKQSBSA-M protochlorophyll a Chemical compound [Mg+2].N1=C2C3=C([N-]4)C(CCC(=O)OC\C=C(/C)CCCC(C)CCCC(C)CCCC(C)C)=C(C)C4=CC(C(=C4C=C)C)=NC4=CC(C(C)=C4CC)=NC4=CC1=C(C)C2=C([O-])C3C(=O)OC DASFNRASQHZIIW-XOTKKQSBSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
HUHWZXWWOFSFKF-UHFFFAOYSA-N uroporphyrinogen-III Chemical compound C1C(=C(C=2CCC(O)=O)CC(O)=O)NC=2CC(=C(C=2CCC(O)=O)CC(O)=O)NC=2CC(N2)=C(CC(O)=O)C(CCC(=O)O)=C2CC2=C(CCC(O)=O)C(CC(O)=O)=C1N2 HUHWZXWWOFSFKF-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
KZTYPOGXRFTJBN-MMLDQJOMSA-N 3-[(3R,12E,21S,22S)-16-ethenyl-11-ethyl-12-(hydroxymethylidene)-3-methoxycarbonyl-17,21,26-trimethyl-4-oxo-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,5(26),6,8,10,13(25),14,16,18(24),19-decaen-22-yl]propanoic acid Chemical compound CCC\1=C2C=C3C(=C4C(=O)[C@@H](C(=C5[C@H]([C@@H](C(=CC6=NC(=CC(=N2)/C1=C/O)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)C(=O)OC)C KZTYPOGXRFTJBN-MMLDQJOMSA-N 0.000 description 1
NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
UJAQYOZROIFQHO-UHFFFAOYSA-N 5-methyl-1,10-phenanthroline Chemical compound C1=CC=C2C(C)=CC3=CC=CN=C3C2=N1 UJAQYOZROIFQHO-UHFFFAOYSA-N 0.000 description 1
NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101500021172 Aplysia californica Myomodulin-C Proteins 0.000 description 1
108091006149 Electron carriers Proteins 0.000 description 1
241000288140 Gruiformes Species 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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 1
241000255777 Lepidoptera Species 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000346285 Ostrinia furnacalis Species 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
210000004102 animal cell Anatomy 0.000 description 1
230000032618 apolysis Effects 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
238000013459 approach Methods 0.000 description 1
235000021405 artificial diet Nutrition 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000015961 delipidation Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000001784 detoxification Methods 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
ZHDBTKPXEJDTTQ-UHFFFAOYSA-N dipyrithione Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-] ZHDBTKPXEJDTTQ-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000003028 elevating effect Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
238000001506 fluorescence spectroscopy Methods 0.000 description 1
238000002189 fluorescence spectrum Methods 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000003897 fog Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000033001 locomotion Effects 0.000 description 1
230000037353 metabolic pathway Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000003595 mist Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000010627 oxidative phosphorylation Effects 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NSFSLUUZQIAOOX-LDCXZXNSSA-N pheophorbide a Chemical compound N1C(C=C2[C@H]([C@H](CCC(O)=O)C(=N2)C2=C3NC(=C4)C(C)=C3C(=O)[C@@H]2C(=O)OC)C)=C(C)C(C=C)=C1C=C1C(C)=C(CC)C4=N1 NSFSLUUZQIAOOX-LDCXZXNSSA-N 0.000 description 1
208000017983 photosensitivity disease Diseases 0.000 description 1
231100000434 photosensitization Toxicity 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
230000037039 plant physiology Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
QBPCOMNNISRCTC-JSSVAETHSA-L protochlorophyllide Chemical group [Mg+2].[N-]1C(C=C2C(=C(CCC(O)=O)C(=N2)C2=C3[N-]C(=C4)C(C)=C3C(=O)[C@@H]2C(=O)OC)C)=C(C)C(C=C)=C1C=C1C(C)=C(CC)C4=N1 QBPCOMNNISRCTC-JSSVAETHSA-L 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
206010037833 rales Diseases 0.000 description 1
230000008439 repair process Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000019832 sodium triphosphate Nutrition 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
235000021127 solid diet Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- 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
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Landscapes

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)
Agricultural Chemicals And Associated Chemicals (AREA)

APAP/P/1989/000112A 1988-01-13 1989-01-13 Porphyric Insecticides AP76A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US14488388A	1988-01-13	1988-01-13

Publications (1)

Publication Number	Publication Date
AP76A true AP76A (en)	1990-03-07

Family

ID=22510566

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
APAP/P/1989/000112A AP76A (en)	1988-01-13	1989-01-13	Porphyric Insecticides
AP88/00112A AP8800112A0 (en)	1988-01-13	1989-02-13	Porphyric insecticides

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
AP88/00112A AP8800112A0 (en)	1988-01-13	1989-02-13	Porphyric insecticides

Country Status (23)

Country	Link
EP (1)	EP0326835B1 (de)
JP (1)	JP2866095B2 (de)
KR (1)	KR890011526A (de)
CN (1)	CN1036688A (de)
AP (2)	AP76A (de)
AT (1)	ATE92712T1 (de)
AU (1)	AU626533B2 (de)
BR (1)	BR8900169A (de)
CA (1)	CA1338855C (de)
DD (1)	DD283317A5 (de)
DE (1)	DE68908195T2 (de)
DK (1)	DK13889A (de)
FI (1)	FI890177L (de)
HU (1)	HUT50179A (de)
IE (1)	IE63488B1 (de)
IL (1)	IL88867A (de)
MA (1)	MA21473A1 (de)
MX (1)	MX170055B (de)
NO (1)	NO890138L (de)
NZ (1)	NZ227505A (de)
PT (1)	PT89440B (de)
YU (1)	YU6789A (de)
ZA (1)	ZA8957B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5242892A (en) *	1984-07-27	1993-09-07	The Board Of Trustees Of The University Of Illinois	Chlorophyll biosynthesis modulators
JP2896963B2 (ja) *	1994-11-28	1999-05-31	株式会社コスモ総合研究所	植物の耐塩性向上剤
US6200974B1 (en)	1997-10-24	2001-03-13	Zeneca Limited	Phenanthroline derivatives
US5916898A (en) *	1997-10-24	1999-06-29	Zeneca Limited	Phenanthroline derivatives
CN101489941A (zh) *	2005-11-10	2009-07-22	耶达研究及发展有限公司	催化处理被卤化有机化合物污染的水
AU2012381990B2 (en)	2012-06-04	2017-02-23	Nutrien Ag Solutions (Canada) Inc.	Formulations containing paraffinic oil and anti-settling agent
WO2014148539A1 (ja)	2013-03-22	2014-09-25	コスモ石油株式会社	５－アミノレブリン酸又はその塩の製造方法
JP2014001224A (ja) *	2013-08-13	2014-01-09	Hatchtech Pty Ltd	外寄生を制御するための組成物および方法
WO2018187845A1 (en) *	2017-04-12	2018-10-18	La Trobe University	Heterocyclic inhibitors of lysine biosynthesis via the diaminopimelate pathway
WO2020150831A1 (en)	2019-01-25	2020-07-30	Suncor Energy Inc.	Photosensitizer compounds, methods of manufacture and application to plants
WO2020163965A1 (en) *	2019-02-15	2020-08-20	Suncor Energy Inc.	Photosensitizer and chelating agent combinations for use as insecticides
CN113677204B (zh)	2019-02-15	2024-03-05	桑科能源股份有限公司	原卟啉ix衍生物改善植物健康的用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE509454C (de) *	1928-11-18	1930-10-09	Bodo Habenicht	Verfahren zur Schaedlingsbekaempfung
NL260511A (de) *	1960-01-26
EP0331211A3 (de) *	1984-07-27	1989-11-23	The Board Of Trustees Of The University Of Illinois	Photodynamische Herbizide

1988
- 1988-12-22 NZ NZ227505A patent/NZ227505A/en unknown
1989
- 1989-01-03 IL IL8886789A patent/IL88867A/en unknown
- 1989-01-04 ZA ZA8957A patent/ZA8957B/xx unknown
- 1989-01-12 NO NO89890138A patent/NO890138L/no unknown
- 1989-01-12 IE IE7689A patent/IE63488B1/en not_active IP Right Cessation
- 1989-01-12 YU YU00067/89A patent/YU6789A/xx unknown
- 1989-01-13 CN CN89101403A patent/CN1036688A/zh active Pending
- 1989-01-13 HU HU89131A patent/HUT50179A/hu unknown
- 1989-01-13 BR BR898900169A patent/BR8900169A/pt not_active Application Discontinuation
- 1989-01-13 DE DE89100605T patent/DE68908195T2/de not_active Expired - Fee Related
- 1989-01-13 EP EP89100605A patent/EP0326835B1/de not_active Expired - Lifetime
- 1989-01-13 DD DD89325032A patent/DD283317A5/de not_active IP Right Cessation
- 1989-01-13 AU AU28498/89A patent/AU626533B2/en not_active Ceased
- 1989-01-13 KR KR1019890000382A patent/KR890011526A/ko not_active Withdrawn
- 1989-01-13 AT AT89100605T patent/ATE92712T1/de not_active IP Right Cessation
- 1989-01-13 FI FI890177A patent/FI890177L/fi not_active Application Discontinuation
- 1989-01-13 DK DK013889A patent/DK13889A/da not_active Application Discontinuation
- 1989-01-13 PT PT89440A patent/PT89440B/pt not_active IP Right Cessation
- 1989-01-13 MX MX014547A patent/MX170055B/es unknown
- 1989-01-13 AP APAP/P/1989/000112A patent/AP76A/en active
- 1989-01-13 JP JP1007533A patent/JP2866095B2/ja not_active Expired - Fee Related
- 1989-01-13 MA MA21714A patent/MA21473A1/fr unknown
- 1989-01-13 CA CA000588241A patent/CA1338855C/en not_active Expired - Fee Related
- 1989-02-13 AP AP88/00112A patent/AP8800112A0/xx unknown

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 108, 1988, 8944s *
CHEMICAL ABSTRACTS, Vol. 75, 1971, 138114u *
CHEMICAL ABSTRACTS, Vol. 80, 1974, 80232s; *

Also Published As

Publication number	Publication date
IL88867A0 (en)	1989-08-15
PT89440B (pt)	1993-09-30
IL88867A (en)	1994-05-30
BR8900169A (pt)	1989-09-12
EP0326835A1 (de)	1989-08-09
DD283317A5 (de)	1990-10-10
CN1036688A (zh)	1989-11-01
ATE92712T1 (de)	1993-08-15
AU626533B2 (en)	1992-08-06
ZA8957B (en)	1990-01-31
NO890138D0 (no)	1989-01-12
YU6789A (en)	1991-02-28
DE68908195D1 (de)	1993-09-16
DK13889A (da)	1989-07-14
IE63488B1 (en)	1995-05-03
JPH02138201A (ja)	1990-05-28
EP0326835B1 (de)	1993-08-11
DE68908195T2 (de)	1994-03-10
MA21473A1 (fr)	1989-10-01
NZ227505A (en)	1992-02-25
PT89440A (pt)	1990-02-08
NO890138L (no)	1989-07-14
KR890011526A (ko)	1989-08-21
JP2866095B2 (ja)	1999-03-08
MX170055B (es)	1993-08-04
AU2849889A (en)	1989-07-20
IE890076L (en)	1989-07-13
FI890177A0 (fi)	1989-01-13
CA1338855C (en)	1997-01-21
AP8800112A0 (en)	1989-02-13
DK13889D0 (da)	1989-01-13
HUT50179A (en)	1989-12-28
FI890177A7 (fi)	1989-07-14
FI890177L (fi)	1989-07-14

Publication	Publication Date	Title
Rebeiz et al.	1988	Porphyric insecticides: 1. Concept and phenomenology
FI116823B (fi)	2006-03-15	Nieltäviä nilviäismyrkkyjä
US5200427A (en)	1993-04-06	Porphyric insecticides
AP76A (en)	1990-03-07	Porphyric Insecticides
JPH05255006A (ja)	1993-10-05	殺虫剤及び殺虫剤の活性を高めるためのスチルベン化合物を含んでなる方法と組成物
US20130296370A1 (en)	2013-11-07	Composition comprising a photoactivatable larvicide
Amor et al.	2000	Porphyrins and related compounds as photoactivatable insecticides. 3. Laboratory and field studies
US5300526A (en)	1994-04-05	Porphyric insecticides
Hedin et al.	1988	Effects of bioregulators on flavonoids, insect resistance, and yield of seed cotton
US7384927B2 (en)	2008-06-10	Alkylated porphyrins as pesticides acting both in the presence and absence of light
Rebeiz et al.	1995	Photodynamics of porphyric insecticides
Wee et al.	2001	Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus
Amor et al.	1998	Porphyrins and related compounds as photoactivatable insecticides I. Phototoxic activity of hematoporphyrin toward Ceratitis capitata and Bactrocera oleae
Rebeiz et al.	1990	Porphyric insecticides: 2. 1, 10-Phenanthroline, a potent porphyric insecticide modulator
DK170932B1 (da)	1996-03-18	Avermectin-derivater, derivaterne til anvendelse ved bekæmpelse af parasitinfektioner hos mennesker og dyr, farmaceutiske præparater indeholdende disse derivater og ikke-terapeutisk fremgangsmåde til bekæmpelse af insekt- eller parasitangreb samt andre avermectin-derivater
US6410567B1 (en)	2002-06-25	Pesticide containing a photosensitizer and an attractant
Bowers	1984	Insect‐Plant Interactions: Endocrine Defences
Pujol‐Lereis et al.	2010	Photosensitizing effect of hematoporphyrin IX on immature stages of Ceratitis capitata (Diptera: Tephritidae)
Robinson et al.	1985	Enhancement of dye-sensitized phototoxicity to house fly larvae in vivo by dietary ascorbate, diazabicyclooctane, and other additives
KR860001567B1 (ko)	1986-10-08	나프탈렌아민 유도체의 제조방법
RU2092053C1 (ru)	1997-10-10	Инсектицидный состав против гусениц тутовой пяденицы
Rebeiz	2013	Porphyric Insecticides
WO2007050867A2 (en)	2007-05-03	Pesticidal compositions and methods of use
WO2006060333A2 (en)	2006-06-08	Insecticidal and nematicidal compositions and methods of use