IL38459A - Phenylacetic acid derivatives,processes for the preparation thereof and insecticidal compositions containing the same - Google Patents
Phenylacetic acid derivatives,processes for the preparation thereof and insecticidal compositions containing the sameInfo
- Publication number
- IL38459A IL38459A IL38459A IL3845971A IL38459A IL 38459 A IL38459 A IL 38459A IL 38459 A IL38459 A IL 38459A IL 3845971 A IL3845971 A IL 3845971A IL 38459 A IL38459 A IL 38459A
- Authority
- IL
- Israel
- Prior art keywords
- group
- compound
- alkenyl
- formula
- alkynyl
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims abstract 3
- 239000000203 mixture Substances 0.000 title claims abstract 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- 241000238631 Hexapoda Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- -1 methylenedioxy Chemical group 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a 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
- A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
1339635 Phenyl acetic acid derivatives SUMITOMO CHEMICAL CO Ltd 16 Dec 1971 [29 Dec 1970] 58483/71 Heading C2C The invention comprises compounds of the formula wherein R 4 is halogen or C 1-4 alkyl, and when more than one of R 4 is present, two such groups may together represent methylenedioxy, n is 0-5, R 1 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 alkynyl, C 3-6 cycloalkyl, benzyl, thienyl or a group of the formula R 2 is C 1-6 alkyl, C 3-6 alkenyl or C 3-6 alkynyl, and A is a group of the formula -COOR 3 or -CH 2 - OR3 where R 3 is C 1-6 alkyl, C 3-6 alkenyl or C 3-6 alkynyl, provided that (1) R 2 is C 3-6 alkynyl when R 3 is C 1-6 alkyl, (2) R 1 is other than thienyl or a group of Formula II when A is CH 2 OR 3 , (3) R 3 is C 4-6 alkenyl or C 4-6 alkynyl when R 1 is a group of Formula II and A is COOR 3 , and (4) R 1 is other than C 1-6 alkyl when A is COOR 3 , wherein R 3 is specifically C 1-6 alkyl. The compounds are prepared by reacting a compound of the formula where X is halogen, hydroxy or OR 2 and Y is CH 2 OH, CH 2 hal, CH 2 OR 3 , COOR 3 or COOH or a reactive derivative thereof, where hal is halogen, with a compound of the formula R 5 Z where Z is hydroxy or halogen and R 5 is R 2 or R 3 , or a reactive derivative thereof. The compounds are used as synergists in insecticidal compositions.
[GB1339635A]
Claims (1)
1. A compound of the formula wher alky l or a gen a halogen atom or an alkyl group having 1 to 4 carbon atoms and n is 1 and A is a group of a cycloalkyl or benzyl when A is a group of alkynyl is a phenyl group and A is a group of A novel compound of the formula wherein is any one of an alkynyl group having from 3 to carbon an alkyl group or an alkenyl group having up to 4 carbon is any one of an alkyl alkenyl group or an alkynyl group having up to 4 carbon when R is an alkynyl group having from 3 to 4 carbon or is any one of an 3 alkenyl group an alkynyl group having from 3 to 4 carbon atoms when is an alkyl group or an alkenyl group having up to 4 carbon is any one of an alkyl an alkenyl group or a cycloalkyl group having up to 6 carbon is a hydrogen a halogen or an alkyl group having from 1 to 4 carbon and n is A compound of the formula claimed in claim wherein is a g a a a thienyl or a phenyl R is a C g a alkenyl or a R is a hydrogen a halogen atom or an alkyl group 4 having 1 to 4 carbon atoms and n is 1 that is a alicynyl 2 when alkynyl when is a phenyl A compound according to claim 3 wherein R is except for compounds benzyl or R is or propargyl and R is claimed in J claim 2 propargyl or A compound of the formula wherein a a cycloalkyl or is a alkenyl or a is a a alkenyl or a that is a when is a halogen or a and n is 39 I V compound of the A compound of the A compound of the A compound of the A compound of the C A process for producing a compound of the formula except for compounds claimed in claim 2 wherein is a a a or is a g a a alkenyl or a ynyl when is a a hydrogen a halogen or an alkyl group having 1 to 4 carbon atoms and n is and A is a group of or provided that is a a a a Δ is a group of is as defined and io a phenyl group and A is a group of which comprises reacting a of the or reactive derivative 41 wherein and n are as defined X is a halogen or is aa defined and Y is is a is as defined or with a compound of the or a reactive derivative wherein Z is hydroxy or a and is the same meanings as or A composition containing an insecticidal compound as hereinbefore defined and as a synergist at least one compound of the formula wherein a a a a thienyl or a phenyl is a Z a is a a alkenyl or a is a hydrogen a halogen or an alkyl group having 1 to 4 carbon atoms and n is that is a alkynyl 42 when is a and A ia a group of or provided that ia a a a a oycloalkyl or benzyl when A a group of defined afad a alkenyl or a alkynyl when ia a phenyl group and A is a group of A prooaaa for producing a of formula 4 n and n aa defined in clala 2 abova vhieh reacting a or a reactlTa derivative represented by the general wherein X any one of xyl a halogen atom or aa defined in claia 2 above with a or a reactive derivative represented by the general V wherein la any one of group or group having the sane aa defined in clala 2 above and Z la any one of hydroxyl group or a halogen for controlling an Insect containing aa an effective ingredient one or two or of a novel phenylacetie acid derivative represented by general formula of claim A method for the control of comprising the application o aa insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45124365A JPS4826223B1 (en) | 1970-12-29 | 1970-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38459A0 IL38459A0 (en) | 1972-02-29 |
| IL38459A true IL38459A (en) | 1976-01-30 |
Family
ID=14883585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38459A IL38459A (en) | 1970-12-29 | 1971-12-27 | Phenylacetic acid derivatives,processes for the preparation thereof and insecticidal compositions containing the same |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4826223B1 (en) |
| BE (1) | BE777362A (en) |
| BR (1) | BR7108620D0 (en) |
| CA (1) | CA958415A (en) |
| CH (1) | CH564904A5 (en) |
| CS (1) | CS161929B2 (en) |
| DE (1) | DE2162598C3 (en) |
| DK (1) | DK130528B (en) |
| ES (1) | ES398339A1 (en) |
| FR (1) | FR2120918A5 (en) |
| GB (1) | GB1339635A (en) |
| HU (1) | HU164975B (en) |
| IL (1) | IL38459A (en) |
| IT (1) | IT945690B (en) |
| NL (1) | NL155534B (en) |
| PH (1) | PH10073A (en) |
| SE (1) | SE393103B (en) |
| ZA (1) | ZA718556B (en) |
-
1970
- 1970-12-29 JP JP45124365A patent/JPS4826223B1/ja active Pending
-
1971
- 1971-12-16 GB GB5848371A patent/GB1339635A/en not_active Expired
- 1971-12-16 DE DE2162598A patent/DE2162598C3/en not_active Expired
- 1971-12-21 PH PH13127A patent/PH10073A/en unknown
- 1971-12-22 ZA ZA718556A patent/ZA718556B/en unknown
- 1971-12-23 CH CH1887171A patent/CH564904A5/xx not_active IP Right Cessation
- 1971-12-23 CA CA131,027A patent/CA958415A/en not_active Expired
- 1971-12-24 ES ES398339A patent/ES398339A1/en not_active Expired
- 1971-12-27 IL IL38459A patent/IL38459A/en unknown
- 1971-12-27 FR FR7146795A patent/FR2120918A5/fr not_active Expired
- 1971-12-27 SE SE7116689A patent/SE393103B/en unknown
- 1971-12-27 CS CS9004A patent/CS161929B2/cs unknown
- 1971-12-28 DK DK640871AA patent/DK130528B/en unknown
- 1971-12-28 BR BR8620/71A patent/BR7108620D0/en unknown
- 1971-12-28 IT IT55055/71A patent/IT945690B/en active
- 1971-12-28 NL NL7117998.A patent/NL155534B/en not_active IP Right Cessation
- 1971-12-28 HU HUSU708A patent/HU164975B/hu unknown
- 1971-12-28 BE BE777362A patent/BE777362A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS161929B2 (en) | 1975-06-10 |
| BE777362A (en) | 1972-04-17 |
| GB1339635A (en) | 1973-12-05 |
| DK130528C (en) | 1975-07-28 |
| PH10073A (en) | 1976-08-05 |
| NL7117998A (en) | 1972-07-03 |
| ES398339A1 (en) | 1975-04-16 |
| IL38459A0 (en) | 1972-02-29 |
| ZA718556B (en) | 1972-09-27 |
| HU164975B (en) | 1974-05-28 |
| CH564904A5 (en) | 1975-08-15 |
| FR2120918A5 (en) | 1972-08-18 |
| DE2162598B2 (en) | 1973-10-31 |
| AU3692071A (en) | 1973-06-21 |
| JPS4826223B1 (en) | 1973-08-07 |
| DE2162598A1 (en) | 1972-07-06 |
| SE393103B (en) | 1977-05-02 |
| NL155534B (en) | 1978-01-16 |
| BR7108620D0 (en) | 1973-06-12 |
| CA958415A (en) | 1974-11-26 |
| IT945690B (en) | 1973-05-10 |
| DE2162598C3 (en) | 1974-05-30 |
| DK130528B (en) | 1975-03-03 |
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