Chlorfenapyr
CAS No. 122453-73-0
 
 

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ACTIVITY: Acaricide, Insecticide (pyrrole)

CAS Name: 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Structure:

 

Note: This pesticide contains both bromine and fluorine; a combination that has the potential to produce severe adverse effects - particularly to the brain.

On January 26, 2005, US EPA approved a Final Rule for tolerances of Chlorfenapyr in or on all food items in food handling establishments where food products are held, processed, and/or prepared at 0.01 ppm as a result of application of chlorfenapyr to crack, crevice and spot applications.

This Final Rule contains a separate document that is EPA's response to FAN's comments on BASF's original petition - see
http://www.fluorideaction.org/pesticides/chlorfenapyr.2005.epa.response.pdf
(
published in EPA Docket, Number: OPP-2004-0362-0002)


Adverse Effects:

Anemia
Body Weight Decrease

Bone
Brain
Cancer: Suggestive - LIVER, TESTES, UTERINE
Cholesterol
CNS
Dermal
Endocrine: Testicular
Endocrine: Uterine
Liver

Spinal Cord

Environmental Effects:

"one of the most reproductively toxic pesticides to avian species [the EPA] has evaluated."

"A persistent compound" in soil and sediment.

Very toxic to fish, aquatic invertebrates, and honeybees, and toxic to algae.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes.
Pending for tolerances for food commodities - See Federal Register below.
US EPA PC Code: 129093
California Chemical Code 3938
US Tolerances: CFR 180.513
FDA LMS Code: B13
Registered use in
(includes only a limited list of countries)

Australia, Japan, Philippines, South Africa, Tanzania, US, Vietnam

Taiwan:
Cabbages, 1.0 ppm
Cantoloups, 0.5 ppm
Leaf vegetables with small leaves, 1.0 ppm
Pears, 0.5 ppm
Peas, 0.5 ppm
Tea, 2.0 ppm
Tomatoes, 0.5 ppm
Wax apples, 0.5 ppm

European Commission: September 5, 2001- European Commission decision to remove from approved substance list.
Japan's Maximum Residue Levels (MRLs)

Apple • Brussels sprouts • Cabbage • Chinese cabbage • Cucumber (including Gherkin) • Cotton seeds • Egg plant • Japanese pear • Japanese persimon • Japanese radish (including Radish root and leaf) • Lettuce (Cos lettuce, Leaf lettuce) • Pear • Strawberry • Sugar beet • Tea • UNSHU orange

Note the exceptionally high level - 50 ppm - for Tea (Green, Black, Oolong, Wulung) -- also note the variation in spelling: Chlorphenapyr.

Mexico: Cottonseed
US Maximum Residue Levels permitted in food commodities  

US FINAL RULE, Sept 26, 2003:
1 ppm in or on raw agricultural commodities - vegetables, fruiting, group 8, which include:
chili, postharvest; pepper, nonbell; tomato, paste; eggplant; pepper, nonbell; sweet tomato, puree; groundcherry; tomatillo; tomato, wet, pomace; pepino; tomato; vegetable, fruiting; pepper; tomato, concentrated products; vegetable, fruiting; grouppepper, bell; tomato, dried pomace

US FINAL RULE, January 26, 2005:
A new tolerance of 0.01 ppm was established January 2005 for residues of chlorfenapyr in or on all food commodities as a result of application of chlorfenapyr to crack, crevice and spot applications in food/feed handling areas where food/feed products are prepared, held, processed, or served .

Other Information
Molecular Formula: C15H11BrCl F3 N2O
Inventing Company: American Cyanamid 
Manufacturers:   BASF,
American Cyanamid
Other Names: Chlorphenapyr, Pirate, Alert, Sunfire, Citrex, Intrepid, Kotetsu,
Pylonga, Stalker, MK-24, Secure,
AC 303, 630,
CL 303630,
241-EUP-128,
241-EUP-141,
241-EUP-142,
241-EUP-143
 
Manufacture site:

US:
Eastman Chemical Co.,
Kingsport, Tennessee 37660

Of special interest:
PAN Data
Material Safety Data Sheets & Labels
Chlorfenapyr Insecticide products - updated November 2003  

October 3, 2005 - New York State registration of Pylon Miticide-Insecticide. (See also, January 16, 2002, NYS registration letter to BASF)

2003 - Comments submitted to US EPA on its Final Rule for food tolerrances of 1 ppm on furiting vegetables, group 8,
published in the Federal Register of September 18, 2003, Docket Number
OPP-2003-0146.
August 11, 2003 -  Comments submitted to US EPA on BASF's petition for food tolerances. These comments were submitted by FAN in response to a petition by BASF which was published in the Federal Register (July 16, 2003). BASF has requested the establishment of a tolerance for residues of chlorfenapyr on all food items in food handling establishments where food products are held, processed, and/or prepared at 0.01 parts per million due to application of chlorfenapyr to crack and crevice and spot applications.

September 17, 2003 - Reply from BASF Corporation to FAN's comments. Also available at US EPA's Docket website. The Docket No. to access these, and other, comments on Chlorfenapyr submitted to US EPA is OPP-2003-0205.
--
Note from FAN: We would appreciate your input on the comments submitted by BASF. Please contact us at pesticides@fluoridealert.org -- Thanks. EC.

Chlorfenapyr Risk Benefit Assessment - EPA Office of Pesticide Programs
August 5, 2005 - The plant and material protection division of Janssen Pharmaceutica NV and BASF Corp. have formed an agreement whereby Janssen may use chlorfenapyr as a pre-construction wood preservative in engineered wood products and on solid timbers. - Chemical Market Reporter.
August 24, 2001 - Summary of Toxicological Data. California EPA. Department of Pesticide Regulation. Medical Toxicology Branch. Also available at: http://www.cdpr.ca.gov/docs/toxsums/pdfs/3938.pdf

March 2000 - US EPA denies the use of Chlorfenapyr (Pirate) on cotton. After completing its review of the pesticide chlorfenapyr (Pirate) for use on cotton, EPA made the determination that chlorfenapyr did not meet the requirements for registration, and in response, American Cyanamid withdrew their Section 3 registration application. This Web site includes the human health and environmental risk assessments and the denial of registration decision memorandum.

EPA Determines That Chlorfenapyr Does Not Meet the Requirements for Registration; American Cyanamid Withdraws Application - EPA Office of Pesticide Programs
Abstracts
March 16, 2000 - American Bird Conservancy press release on EPA decision to deny cotton registration.
April 30, 1999 - Request to EPA to Deny Chlorfenapyr Use - Letter to EPA from Deputy Director of Fish and Wildlife Service, John G. Rogers Jr
September 16, 1999 - Higher Tier Ecological Risk Assessment for Chlorfenapyr. FIFRA Scientific Advisory Panal Meeting. SAP Report No. 99-04C.
Jan 23, 1998 - EPA's Lynn Goldman on "The Impact of the 1996 Food Quality Protection Act on Louisiana Growers." - Note that both spelling variations (Chlorfenapyr / Chlorphenapyr) are cited.
Oct 1999 - PIRATE FEAR: Controversy heats up about chlorfenapyr, a.k.a. Pirate--a pesticide some claim is the next DDT - Scientific American
June 2, 1999 - EPA Decides Not to Approve Use of Chlorfenapyr - Chemical Week
April 30, 1996 - Press release of launch of new insecticide called Kotetsu. Mitsubishi Chemical Corp.
2002 - NIPON SODA ANNUAL REPORT 2002 - cites the following organofluorine pesticides and their product names: Chlorfenapyr * Fluacrypyrim * Fluazinam * Fluvalinate * Triflumizole
Aug 2001 - IR-4 - New Products/Transitional Solution List - This list contains brief descriptions of numerous new pest control materials that have been introduced over the last several years. Additionally, it contains information on some "older" crop protection chemicals that are believed to have room for new uses. This List includes Chlorfenapyr
April 2000 - Food and Drug Administration Pesticide Residue Monitoring. Table 3. Pesticides detectable by methods used in 1999 regulatory monitoring.
Oct 2001 - Glossary of Pesticide Chemicals. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration.

Table D2: Details of Residues Exceeding non-harmonised MRLs,
including national MRLs

Surveillance sampling
Reporting country: Germany
Year of sampling: 2003
http://www.bvl.bund.de/lebensmittel/dateien/eg03-642d2_v2.pdf
Pesticide Food item Point of sampling (*) Country of origin Residue in mg/kg national MRL (mg/kg) Follow-up (**)
chlorfenapyr Peppers R NL 0.02 0.01 - 
chlorfenapyr Peppers O ES 0.013 0.01 -  
chlorfenapyr Peppers R ES 0.017 0.01 -  
chlorfenapyr Peppers O ES 0.02 0.01 -  
chlorfenapyr Peppers R ES 0.038 0.01 -  
chlorfenapyr Peppers O ES 0.039 0.01 -  
chlorfenapyr Peppers O ES 0.04 0.01 A
chlorfenapyr Peppers R ES 0.06 0.01 -  
chlorfenapyr Peppers O ES 0.063 0.01 -  
chlorfenapyr Peppers R ES 0.082 0.01 -  
chlorfenapyr Peppers R ES 0.15 0.01 -  
chlorfenapyr Peppers O ES 0.15 0.01 A
chlorfenapyr Peppers R ES 0.15 0.01 A
chlorfenapyr Peppers O ES 0.22 0.01 A
chlorfenapyr Peppers W TR 0.03 0.01 -  
chlorfenapyr Peppers O TR 0.12 0.01 -  
chlorfenapyr Peppers O QU 0.04 0.01 A
chlorfenapyr Peppers R QU 0.08 0.01 -  
chlorfenapyr Peppers R QU 0.09 0.01 -  

(*) Point of sampling in distribution: F = farmgate, R = retail, W = wholesale, O = other

(**) A: Administrative consequences have followed, e.g. prohibiting for sale, prosecutions, the levying of penalties or fines

These explanatory notes are cited at http://www.bvl.bund.de/lebensmittel/dateien/eg03-642d1_v2.pdf


Chlorfenapyr. Chemical qualifying for PIC notification.
http://ecb.jrc.it/edex/annex_1g.php?value='122453-73-0b'

A little background to the
Rotterdam Convention Prior Informed Consent (PIC)

Toxic pesticides and other hazardous chemicals kill or seriously sicken thousands of people every year. They also poison the natural environment and damage many wild animal species. Governments started to address this problem in the 1980s by establishing a voluntary Prior Informed Consent procedure. PIC required exporters trading in a list of hazardous substances to obtain the prior informed consent of importers before proceeding with the trade.
 
In 1998, governments decided to strengthen the procedure by adopting the Rotterdam Convention, which makes PIC legally binding. The Convention establishes a first line of defense by giving importing countries the tools and information they need to identify potential hazards and exclude chemicals they cannot manage safely. If a country agrees to import chemicals, the Convention promotes their safe use through labeling standards, technical assistance, and other forms of support. It also ensures that exporters comply with the requirements.
 
The Rotterdam Convention entered into force on 24 February 2004.

The Parties are: Armenia, Austria, Belgium, Benin, Bolivia, Bulgaria, Burkina Faso, Cameroon, Canada, Côte d’Ivoire, Czech Republic, Denmark, El Salvador, Equatorial Guinea, Ethiopia, European Community, Gabon, Gambia, Germany, Ghana, Greece, Guinea, Hungary, Italy, Jamaica, Jordan, Kyrgyzstan, Latvia, Libyan Arab Jamahiriya, Luxembourg, Malaysia, Mali, Marshall Islands, Mongolia, Netherlands, New Zealand, Nigeria, Norway, Oman, Panama, Paraguay, Republic of Korea, Romania, Rwanda, Samoa, Saudi Arabia, Senegal, Slovenia, South Africa, Suriname, Sweden, Switzerland, Syrian Arab Republic, Thailand, Ukraine, United Arab Emirates, United Republic of Tanzania and Uruguay.

See http://www.pic.int/


Chlorfenapyr is the first commercial pesticide to be derived from a class of microbially-produced compounds known as halogenated pyrroles.  Synthesized in 1988 from a naturally-produced chlorinated pyrrole, chlorfenapyr (AC 303,630 Technical: 4-bromo-2-(4-chlorophenyl)-1-(ethosymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) is being used in at least 32 countries, including the United States.  Chlorfenapyr is a 'proinsecticide', i.e., it requires activation through metabolism. The parent compound is converted to a metabolite, which functions as an uncoupler of oxidative phosphorylation at mitochondria.The primary, and most toxic, metabolite is the N-dealkylated compound AC 303,268 (Fig. 1).Chlorfenapyr has low volatility and water solubility; is lipophilic; binds strongly to soil particles; and degrades slowly in soil (avg. half life of` 1 yr), sediment (avg. half life of 1.1 yr), and water (avg. half life of 0.8 yr).
Ref: Effects of Chlorfenapyr on Adult Birds, Patuxent Wildlife Research Center.
Compound AC 303,268


Comment from the Environmental Working Group
http://www.ewg.org/pub/home/reports/killerweeds/killer-4.html

Chlorfenapyr is an insecticide... developed by American Cyanamid, a subsidiary of the international chemical giant American Home Products. This pesticide kills bug by disrupting enzymes in their mitochondria, the part of the cell that turns food into energy. Although there are few known risks to humans from the chemical at this time, there is mounting evidence chlorfenapyr can affect other animals in the same way that it affects insects and could have significant impacts on migratory bird populations. Like DDT, chlorfenapyr persists in soil and water for a long time, disrupting the environment years after it is sprayed on crops. According to Edward Sones, a German chemical industry scientist, "I would never consider even continuing research on compounds representing this level of environmental hazard" (Williams 1999).

American Cyanamid recently petitioned the EPA to allow the use of chlorfenapyr in homes and schools and hopes to be able to spray the pesticide on dozens of other crops, including foods eaten by children like apples, in the coming years. Over 45,000 pounds of chlorfenapyr were used on cotton under Section 18 exemptions in 1998 according to the U.S. Department of Agriculture (USDA 1999). The Section 18 program is a fraud that has mushroomed far beyond the legitimate need to help farmers control emergency pest infestations. The program has little to do with real pest emergencies and has become a test marketing program for pesticide companies through which they avoid the full children's health requirements of FQPA. Children bear the risk of the untested pesticides, while pesticide companies reap the profits. Nothing better illustrates the phony essence of the program than the surge in emergency and crisis exemptions granted for control of weeds.


AUSTRALIA NEW ZEALAND FOOD AUTHORITY (ANZFA):
SUMMARY OF REQUESTED MRLS FOR APPLICATION A447 (page 35-36)

Chlorfenapyr
Food
MRL
(mg/kg)
Information
Cotton seed Delete
Substitute
T0.5
0.5

The chemical is used to control Heliothis spp on cotton.

 

 

 

 

 

 

 

NEDI = 2.37% of ADI

Edible offal (Mammalian) Delete
Substitute
T0.1
*0.05
Eggs Delete
Substitute
T*0.01
*0.01
Meat (mammalian) (in the fat) Delete
Substitute
T0.1
0.05
Milks Delete
Substitute
T*0.01
*0.01
Poultry, Edible offal of Delete
Substitute
T*0.01
*0.01
Poultry meat (in the fat) Delete
Substitute
T0.02
*0.01
T = Indicates the MRL is temporary for a period of time and subject to revision following review of additional data.
* = MRL is set at or about the limit of quantification.
NEDI = National Estimated Dietary Intake.
ADI = Acceptable Daily Intake.
Ref: May 8, 2002. Final Assessment Report [Inquiry - S.17]. Application A447. Maximum Residue Limits. ANZFA. Australia New Zealand Food Authority. Also Available at:
http://www.fluorideaction.org/pesticides/australia.mrls.may.8.2002.pdf

AUSTRALIA NEW ZEALAND FOOD AUTHORITY (ANZFA):
8.5.4 Imported Foods. The following are the quantities of foods that have been imported into Australia in 1999 and 2000. This data are for foods for which reductions and deletions of MRLs are proposed.

Chlorfenapyr 1999 2000
Edible offal (Mammalian) 419 tonnes 484 tonnes
Meat (Mammalian) (in the fat) 2,627 tonnes 4,817 tonnes
Poultry meat 14 tonnes 14 tonnes
Ref: May 8, 2002. Final Assessment Report [Inquiry - S.17]. Application A447. Maximum Residue Limits. ANZFA. Australia New Zealand Food Authority. Also available at:
http://www.fluorideaction.org/pesticides/australia.mrls.may.8.2002.pdf


2002 - Pesticide residues were investigated in 8 of 38 kinds of domestic vegetables and 3 of 25 kinds of domestic fruits on the Tokyo market in 2001. Thirty kinds of pesticides such as organophosphorines(EPN,etc.), organochlorines(endsulfans, etc.), carbamate (methomyl), organonitrogens(dichrofluanid, etc.), pyrethroids(acrinathrin, etc.) and others (including chlorfenapyr) were detected in 7 of 26 kinds of domestic vegetables (detection rate : 68%). Their concentrations were between tr. (below 0.01 ppm) and 0.93 ppm...

Survey of Pesticide Residues in Domestic Vegetables and Fruits (2001.4-2002.3)
Authors: Ichiro TAKANO, Toshihiro NAGAYAMA, Maki KOBAYASHI, Yasuhiro TAMURA, Sanae TOMIZAWA, Yukinari TATEISHI, Naoko KIMURA, Kyoko KITAYAMA, Kazuo SAITO


US Federal Register

•• Note: Due to length, the following is a partial list. Click here to see full list of FR entries.

Date Published Docket Identifiction Number Details
Jan 26, 2005 OPP-2004-0362 BASF - Pesticide Tolerance. FINAL RULE. This regulation establishes a tolerance for residues of chlorfenapyr in or on all foods at 0.01 parts per million (ppm) except fruiting vegetables.

This Final Rule contains a separate document that is EPA's response to FAN's comments - see
http://www.fluorideaction.org/pesticides/chlorfenapyr.2005.epa.response.pdf

(
published in EPA Docket, Number: OPP-2004-0362-0002)

Aug 11, 2003: FAN's comments on BASF's petition for this tolerance at
http://www.fluorideaction.org/pesticides/chlorfenapyr.comments.aug03.htm

Sept 17, 2003: BASF's response to FAN's comments at
http://www.fluorideaction.org/pesticides/chlorfenapyr.basf.sept.2003.pdf

The nature of the toxic effects caused by chlorfenapyr are discussed in a September 26, 2003, Final Rule - see comments immediately below.

See BASF's petition (July 16, 2003) for this Tolerance at
http://www.fluorideaction.org/pesticides/chlorfenapyr.fr.july16.2003.htm

•• Conditions for this Final Rule: A developmental neurotoxicity study to determine the cause/relationship
of potential central nervous system/myelinopathic alterations to neurotoxicity in the developing young. This condition was stated in the September 26, 2003, Federal Register, and referred to in this Final Rule.

Sept 26, 2003

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

OPP-2003-0146

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

BASF - Pesticide Tolerance. FINAL RULE. This regulation establishes a tolerance for residues of chlorfenapyr at 1.0 ppm in or on vegetables, fruiting, group 8, grown in greenhouses. BASF Agro Research, now BASF Corporation requested this tolerance. In the FR of September 13, 2000, EPA announcied the filing of an amended pesticide petition (PP 6F4716) by BASF Agro Research, now BASF Corporation.
-- MRID No. 42770219 (1993)-- 90-Day oral toxicity rats. NOAEL = 24.1 mg/kg/day. LOAEL = 48.4, based on spongiform myelopathy in the brain and spinal cord of male rats, decreased body weight gain and increased relative liver weight in males and females, increased absolute liver weight in females, and decreased hemoglobin in females.
-- MRID No.
43492830 (1994). 90-Day oral toxicity mouse . NOAEL = 27.6/40, M/F. LOAEL = 62.6/78, M/F, based on reduced body weights/body weight gains, and spongiform encephalopathy in both sexes.
-- MRID No. 42770220 (1993). 90-Day oral toxicity dog. NOAEL = 3.9/4.5 mg/kg/ day, M/F. LOAEL = 6.7/6.8 mg/kg/ day, M/Fbased on emaciation, decreased body weight gains, and decreased food efficiency.
-- MRID No. 43492831 (1993). 21/28-Day dermal toxicity rabbit. NOAEL = 100 mg/kg/day. LOAEL = 400 mg/kg/day, for both sexes, based on changes in liver chemistry and morphology.
-- MRID No. 42884202 (1993). Prenatal developmental rat. Maternal NOAEL = 25 mg/kg/day, based on decreased body weight gain and relative food consumption during treatment Developmental NOAEL >=225 mg/kg/day. Developmental LOAEL = not identified.
-- MRID No. 42770222 (1993).
Prenatal developmental rabbit. Maternal NOAEL = 5 mg/kg/day. Maternal LOAEL = 15 mg/ kg/day, based on decreased body weight gain during treatment Developmental NOAEL = 15 mg/kg/day Developmental LOAEL = 30 mg/kg/day, based on increased post implantation loss.
-- MRID No. 43492836 (1994). 2-Generation reproduction and fertility effects rat. Parental systemic NOAEL = 4.4-4.5 mg/kg/day, M. Parental systemic LOAEL = 22.2-22.5 mg/kg/day, M, based on decreased absolute body weight/body weight gains of P1
males during premating. Offspring systemic NOAEL = 4.4-5.1 mg/kg/day. Offspring systemic LOAEL = 22.2-25.6 mg/kg/day, based on decreased pup weights at weaning. Reproductive NOAEL >=44- 50.7 mg/kg/day. Reproductive LOAEL: not identified.
-- MRID No.
43492834 (1994). Chronic toxicity dog. NOAEL = 4.0/4.5 mg/kg/day, M/F. LOAEL = 8.7/10.1 mg/kg/ day, M/F, based on decreased body weight/body weight gains.
-- MRID No. 43492838 (1994). Carcinogenicity mouse. NOAEL = 2.8/3.7 mg/kg/day, M/F. LOAEL = 16.6/21.9 mg/kg/day, M/F, based on decreased body weight gains, brain vacuolation, and scabbing of the skin (males) No evidence of carcinogenicity.
-- MRID No.
43492837 (1994). Combined chronic/ carcinogenicity in rat. NOAEL = 15 mg/kg/day, males. LOAEL = 30.8 mg/kg/day, males, based on anemia. NOAEL = 3.6 mg/kg/day, females LOAEL = 18.6 mg/kg/day, females, based on decreased body weight/ body weight gain. Classification: ``Suggestive Evidence of Carcinogenicity, but Not Sufficient to Assess Human Carcinogenic Potential'' based on significant trends in liver tumors (adenomas and combined adenomas/ carcinomas), malignant histiocytic sarcomas, and testicular cell tumors in male rats and uterine polyps in female rats seen at the highest dose.
-- MRID No. 43492833 (1994). Chronic neurotoxicity rat. NOAEL = 2.6/3.4 mg/kg/day, M/F. LOAEL = 13.6/18 mg/kg/ day, M/F, based on the presence of myelinopathic alterations in the central nervous system (CNS) in male rats and decreased average body weights/body weight gains, food efficiency, absolute food consumption (females) and water consumption (males)
-- Developmental toxicity study - rabbit. LOAEL = 30 mg/kg/day based on increased post-implantation loss
-- Acute neurotoxicity study - rat. LOAEL = 90 mg/kg/day based on lethargy in male rats.
-- Chronic neurotoxicity study - rat. LOAEL = 13.6/18 mg/kg/ day, M/F, based on the presence of myelinopathic alterations in the CNS in male rats and decreased average body weights, body weigh gains, food efficiency, absolute food consumption (F), and water consumption (M) Supporting this endpoint are similar CNS lesions and skin lesions observed in the mouse carcinogenicity study (NOAEL = 2.8).
-- The most highly exposed population subgroup is children 1-2 years old, at 47% of the cPAD.
-- EPA concluded that a FQPA SF in the form of UFDB of 10X is required until the data from the DNT study are received and evaluated.

-- Conditions: A developmental neurotoxicity study to determine the cause/relationship of potential central nervous system/myelinopathic alterations to neurotoxicity in the developing young.

•• Note: Due to length, the above is a partial list. Click here to see full list of FR entries.

 
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