DE2739098C2 - - Google Patents
Info
- Publication number
- DE2739098C2 DE2739098C2 DE2739098A DE2739098A DE2739098C2 DE 2739098 C2 DE2739098 C2 DE 2739098C2 DE 2739098 A DE2739098 A DE 2739098A DE 2739098 A DE2739098 A DE 2739098A DE 2739098 C2 DE2739098 C2 DE 2739098C2
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- hydrazone
- bis
- pentadien
- tetrahydro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- -1 alpha, alpha, alpha-trifluoro-p-tolyl Chemical group 0.000 claims description 8
- KKVCZNHIJHTDFP-YDWXAUTNSA-N (1e,4e)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)\C=C\C1=CC=C(Cl)C=C1 KKVCZNHIJHTDFP-YDWXAUTNSA-N 0.000 claims description 3
- IQVNEKKDSLOHHK-UHFFFAOYSA-N hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(C=CC=1C=CC(=CC=1)C(F)(F)F)C=CC1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- CCNADQHLBCFRKR-UHFFFAOYSA-N n-[1,5-bis(4-chlorophenyl)penta-1,4-dien-3-ylideneamino]-5-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(Cl)=CC=C1C=CC(C=CC=1C=CC(Cl)=CC=1)=NNC1=NCC(C=2C=CC=CC=2)N1 CCNADQHLBCFRKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- DIUOFYPIMRHLCY-UHFFFAOYSA-N n-[1,5-bis(4-chlorophenyl)penta-1,4-dien-3-ylideneamino]-4,5,6,7-tetrahydro-1h-1,3-diazepin-2-amine Chemical compound C1=CC(Cl)=CC=C1C=CC(C=CC=1C=CC(Cl)=CC=1)=NNC1=NCCCCN1 DIUOFYPIMRHLCY-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 25
- 241000257303 Hymenoptera Species 0.000 description 15
- 241000256244 Heliothis virescens Species 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 240000002024 Gossypium herbaceum Species 0.000 description 9
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FYYNLEVGNLTRGJ-UHFFFAOYSA-N NN=C(C)C=C=C Chemical compound NN=C(C)C=C=C FYYNLEVGNLTRGJ-UHFFFAOYSA-N 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000037406 food intake Effects 0.000 description 5
- 235000012631 food intake Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 235000021400 peanut butter Nutrition 0.000 description 3
- OIUBVYQZMUKRRF-UHFFFAOYSA-N 1,5-bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C=CC(=O)C=CC1=CC=C(C(F)(F)F)C=C1 OIUBVYQZMUKRRF-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000736128 Solenopsis invicta Species 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- TUXLNOCPYMQUEU-UHFFFAOYSA-N (3,3-dimethyl-2,4-dihydro-1H-pyridin-6-yl)hydrazine hydroiodide Chemical compound I.CC1(C)CNC(NN)=CC1 TUXLNOCPYMQUEU-UHFFFAOYSA-N 0.000 description 1
- 241000958610 Acromyrmex versicolor Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241000722666 Camponotus Species 0.000 description 1
- 241001491934 Camponotus pennsylvanicus Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 241001507629 Formicidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001638457 Lasius alienus Species 0.000 description 1
- 241000283797 Lasius interjectus Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- RKBBWHSAGYYZSZ-UHFFFAOYSA-N NN=C(C=C)C=C Chemical class NN=C(C=C)C=C RKBBWHSAGYYZSZ-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241000958652 Solenopsis molesta Species 0.000 description 1
- 241001415041 Solenopsis richteri Species 0.000 description 1
- 241001221807 Solenopsis xyloni Species 0.000 description 1
- 241001374808 Tetramorium caespitum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- QXBORBIAQOMSLR-UHFFFAOYSA-N n-[1,5-bis(4-chlorophenyl)penta-1,4-dien-3-ylideneamino]-5,5-dimethyl-4,6-dihydro-1h-pyrimidin-2-amine Chemical compound C1C(C)(C)CNC(NN=C(C=CC=2C=CC(Cl)=CC=2)C=CC=2C=CC(Cl)=CC=2)=N1 QXBORBIAQOMSLR-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent 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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ZA00774965A ZA774965B (en) | 1977-08-16 | 1977-08-16 | Pentadienone hydrazones as insecticides |
DE19772739098 DE2739098A1 (de) | 1977-08-16 | 1977-08-30 | Pentadienonhydrazon und insekticid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ZA00774965A ZA774965B (en) | 1977-08-16 | 1977-08-16 | Pentadienone hydrazones as insecticides |
DE19772739098 DE2739098A1 (de) | 1977-08-16 | 1977-08-30 | Pentadienonhydrazon und insekticid |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2739098A1 DE2739098A1 (de) | 1979-03-08 |
DE2739098C2 true DE2739098C2 (en:Method) | 1989-04-27 |
Family
ID=25772639
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19772739098 Granted DE2739098A1 (de) | 1977-08-16 | 1977-08-30 | Pentadienonhydrazon und insekticid |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE2739098A1 (en:Method) |
ZA (1) | ZA774965B (en:Method) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1393686A1 (en) * | 2002-08-30 | 2004-03-03 | Smiths Group plc | Oocyte and embryo handling apparatus regulating the temperature within a tube |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3878201A (en) * | 1971-04-05 | 1975-04-15 | American Cyanamid Co | 1,5-Bis substituted-1,4-pentadien-3-one substituted amidinohydrazone salts and method of preparing the same |
-
1977
- 1977-08-16 ZA ZA00774965A patent/ZA774965B/xx unknown
- 1977-08-30 DE DE19772739098 patent/DE2739098A1/de active Granted
Also Published As
Publication number | Publication date |
---|---|
ZA774965B (en) | 1978-06-28 |
DE2739098A1 (de) | 1979-03-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
8110 | Request for examination paragraph 44 | ||
8125 | Change of the main classification |
Ipc: C07D239/18 |
|
AG | Has addition no. |
Ref country code: DE Ref document number: 2908651 Format of ref document f/p: P |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition |