Carbendazim

Iupac Name：methyl N-(1H-benzimidazol-2-yl)carbamate

Molecular Weight：191.18700

Modify Date.: 2022-11-11 00:43

Introduction: White Solid Colorless crystalline solid or light-gray powder. Commercially supplied as dry concentrate that ismixed with water for spraying.ChEBI: A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomyetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarb View more+

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1. Names and Identifiers

1.1 Name: Carbendazim
1.2 Synonyms: 1h-benzimidazol-2-ylcarbamicacidmethylester 1h-benzimidazol-2-yl-carbamicacimethylester 1h-benzimidazole-2-carbamic acid methyl ester 2-(Methoxycarbonylamino)benzimidazde 2-(methoxy-carbonylamino)-benzimidazol a118 agrizim BCM BCM,Carbendazim,Methyl 2-benzimidazolecarbamate BCM,Methyl 2-benzimidazolecarbamate,Methyl benzimidazol-2-ylcarbamate bmk Carbamic acid, N-1H-benzimidazol-2-yl-, methyl ester carbendazol EINECS 234-232-0 Fenbendazole impurity A MBCA mecarzole Methanol, 1-(1H-benzimidazol-2-ylimino)-1-methoxy-, (E)- methyl 1H-1,3-benzimidazol-2-ylcarbamate Methyl 1H-benzimidazol-2-ylcarbamate methyl benzimidazol-2-ylcarbamate Methyl hydrogen 1H-benzimidazol-2-ylcarbonimidate methyl N-1H-benzimidazol-2-ylcarbamate MFCD00055390 myco spin Stein T56 BM DNJ CMVO1

1.3 CAS No.: 10605-21-7

1.4 CID: 25429

1.5 EINECS(EC#): 234-232-0

1.6 Molecular Formula: C9H9N3O2 (isomer)

1.7 Inchi: InChI=1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)

1.8 InChkey: TWFZGCMQGLPBSX-UHFFFAOYSA-N

1.9 Canonical Smiles: COC(=O)NC1=NC2=CC=CC=C2N1

1.10 Isomers Smiles: COC(=O)NC1=NC2=CC=CC=C2N1

2. Properties

2.1 Density: 1.421g/cm3

2.1 Melting point: >300°C(lit.)

2.1 Boiling point: 409ºC

2.1 Refractive index: 1.6500 (estimate)

2.1 Flash Point: 11°C

2.1 Precise Quality: 191.06900

2.1 PSA: 67.01000

2.1 logP: 1.81420

2.1 Solubility: pyridine: soluble1%, clear, very faintly brownish-yellow

2.2 Appearance: Light gray or beige powder

2.3 Chemical Properties: White Solid

2.4 Color/Form: Light-gray powder.
White solid /Technical Grade/

2.5 pKa: 4.48(at 25℃)

2.6 Water Solubility: <0.1 g/100 mL at 21 oC

2.7 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Agricultural Uses: Fungicide: Carbendazim is a systemic fungicide used as a drench to control a broad range of fungi in cereals, vegetables, oilseed rape, sugar beets, grapes, tomatoes, pome fruit and stone fruit. It is also used in post-harvest storage and as treatment in seed pre-planting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch elm disease.

3.2 Definition: ChEBI: A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomyetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.

3.3 General Description: Light gray or beige powder.

3.4 Potential Exposure: Carbendazim is a benzimidazole/carbamate systemic fungicide used as a drench to control abroad range of fungi in cereals, vegetables, oilseed rape,sugar beets, grapes, tomatoes, pome fruit, and stone fruit. Itis also used in postharvest storage and as treatment in seedpreplanting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch Elmdisease.

3.5 Shipping: UN3082 Environmentally hazardous substances,liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

3.6 Usage: Is a fungicide.

3.7 Waste Disposal: Do not discharge into drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration witheffluent gas scrubbing is recommended. Containers must bedisposed of properly by following package label directionsor by contacting your local or federal environmental controlagency, or by contacting your regional EPA office. Carbendazim Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Symbol: GHS08;GHS09;

4.1 Hazard Codes: T

4.1 Signal Word: DANGER

4.1 Risk Statements: R46; R60; R61; R50/53

4.1 Safety Statements: S53-S45-S60-S61-S36/37

4.1 Octanol/Water Partition Coefficient: log Kow = 1.52

4.2 Fire Hazard: Literature sources indicate that Carbendazim is probably nonflammable.

4.3 Other Preventative Measures: SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

4.4 Hazard Declaration: H340; H360FD; H410

4.4 Cleanup Methods: Solid spillage should be picked up with an industrial vacuum cleaner and disposed of in accordance with local regulations.

4.5 DisposalMethods: Must be disposed of by special means, e.g., suitable incineration, in accordance with local regulations. [40 CFR 240-280, 300-306, 702-799 (7/1/2002)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U372, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

4.6 RIDADR: UN 3077 9/PG 3

4.6 Safety Profile: Moderately toxic by skin contact. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. An agricultural chemical and pesticide. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

4.7 Caution Statement: P201-P273-P308 + P313-P501

4.7 Formulations/Preparations: Acidazim; Amibendazim; Bendazim; Mobeedazim; Carbendate; Cekudazim; Chemzim; Chemcarb; Tartan; Devistin; Dhanustin; Ranger; Carbenex; Agni; Eurozim-50; Fertidazim; Takistin; Benfil; Hilzim; Curacarb; Arrest; Micfun; Attention; Laicar; Carzim; Luxazim-F; Majestin; Mitrosal; Sharp; Pacarzim; Volzim; Carbenzim; Sicostin, Fungy; Protek; Unisol; Vicarben; Zen.
Aqueous suspension, water dispersible granules and a wettable powder.
Discontinued Names: Mastiff; Ponnax; Corbel Triple; Corbel Duo; Bavistin; Bavical; Bavical F; Cosmic; Prodazim; Occidor Plus; Raydor; Delsene; Delsene M; Bolda; Kombat; Masolon; Bravocarb; Azidro; Akozim; Silcarbon; Silear.
Derosal (AgrEvo)
Carbate (Pan Brittanica)
Cekudazim (Cequisa)
... Available in wettable powder formulations or dispersions that contain from 6-70% active ingredient, the balance is either inert ingredients or other fungicides.
USEPA/OPP Pesticide Code 128872; Trade Names: E-965; BAS 3460; Derosal; Kemdazin; U-32.104; Equitdazin; and Pillarstin.
FB642(methyl-2-benzimidazolecarbamate, carbendazim) [Hammond LA et al; J Cancer Res Clin Oncol 127(5): 301-13 (2001)] PubMed Abstract

4.8 Incompatibilities: Carbamates are incompatible with reducing agents, strong acids, oxidizing acids, peroxides, andbases. Contact with active metals or nitrides cause the releaseof flammable, and potentially explosive, hydrogen gas.

4.9 WGK Germany: 3

4.9 RTECS: DD6500000

4.9 Reactivities and Incompatibilities: Compatible with many other pesticides, but incompatible with alkaline materials.

4.10 Safety: Safety Information about?Carbendazim (CAS NO.10605-21-7):
Hazard Codes:?T,N,F
Risk Statements: 46-60-61-50/53-39/23/24/25-11?
R11: Highly flammable.?
R46: May cause heritable genetic damage.?
R60: May impair fertility.?
R61: May cause harm to the unborn child.?
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
Safety Statements: 53-45-60-61-36/37
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S53: Avoid exposure - obtain special instructions before use.?
S60: This material and its container must be disposed of as hazardous waste.?
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: DD6500000

4.11 Specification: ?Carbendazim (CAS NO.10605-21-7) is a carbamate ester-amine. Amines behave as chemical bases. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

4.12 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LD50	oral	1800mg/kg (1800mg/kg)	?	Indian Journal of Pharmacology. Vol. 18, Pg. 102, 1986.
dog	LD50	oral	> 2500mg/kg (2500mg/kg)	?	Pesticide Manual. Vol. 9, Pg. 123, 1991.
guinea pig	LD50	oral	4150mg/kg (4150mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(3), Pg. 58, 1987.
mouse	LD50	intraperitoneal	1225mg/kg (1225mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(3), Pg. 58, 1987.
mouse	LD50	oral	7700mg/kg (7700mg/kg)	AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(5), Pg. 49, 1981.
quail	LD50	oral	> 10gm/kg (10000mg/kg)	?	Pesticide Manual. Vol. 9, Pg. 123, 1991.
rabbit	LD50	oral	8160mg/kg (8160mg/kg)	BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(3), Pg. 58, 1987.
rabbit	LD50	skin	8500mg/kg (8500mg/kg)	?	Indian Journal of Pharmacology. Vol. 18, Pg. 102, 1986.
rat	LD50	intraperitoneal	1720mg/kg (1720mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(3), Pg. 58, 1987.
rat	LD50	oral	6400mg/kg (6400mg/kg)	?	"Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 4, Pg. 131, 1976/1977.
rat	LD50	skin	2gm/kg (2000mg/kg)	?	"Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 1B

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H340 May cause genetic defects H410 Very toxic to aquatic life with long lasting effects H360FD
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

7. Other Information

7.0 Merck: 13,1799

7.1 BRN: 649044

7.2 Chemical Properties: White Solid

7.3 Chemical Properties: Colorless crystalline solid or light-gray powder. Commercially supplied as dry concentrate that is mixed with water for spraying.

7.4 Uses: Is a fungicide.

7.5 Definition: ChEBI: A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomy etes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.

7.6 Uses: Fungicide.

7.7 General Description: Light gray or beige powder.

7.8 Air & Water Reactions: Insoluble in water. Carbendazim slowly decomposes in alkaline solution. .

7.9 Reactivity Profile: Carbendazim is a carbamate ester-amine. Amines behave as chemical bases. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

7.10 Health Hazard: ACUTE/CHRONIC HAZARDS: When heated to decomposition Carbendazim emits toxic fumes of NOx.

7.11 Fire Hazard: Literature sources indicate that Carbendazim is probably nonflammable.

7.12 Agricultural Uses: Fungicide: Carbendazim is a systemic fungicide used as a drench to control a broad range of fungi in cereals, vegetables, oilseed rape, sugar beets, grapes, tomatoes, pome fruit and stone fruit. It is also used in post-harvest storage and as treatment in seed pre-planting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch elm disease.

7.13 Trade name: ABACOL®; AIMCOZIM; BAS® 3460; BAS® 67054; BATTAL®; BAVISTIN®; BENDAZIM®; CARBATE®; CARBENDAZIME®; CARBENDAZOL®; CARBENDAZOLE®; CARBENDAZYM®; CARBENDOR; CEKUDAZIM®; CORBEL; CTR® 6669; CUSTOS®; DEFENSOR®; DELSENE®; DEROSAL®; E-965®; DERROPRENE®; EQUITDAZIN®; FUNGISOL®; HOE 17411®; LIGNASAN®; IMISOL®; KEMDAZIN®; MERGAL®; PILLARSTIN®; POLYPHASE®; RODAZIM®; STEMPOR®; SUPERCARB, TRITICOL®; TRITICOL®; U-32.104®

7.14 Safety Profile: Moderately toxic by skin contact. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. An agricultural chemical and pesticide. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

7.15 Potential Exposure: Carbendazim is a benzimidazole/carbamate systemic fungicide used as a drench to control a broad range of fungi in cereals, vegetables, oilseed rape, sugar beets, grapes, tomatoes, pome fruit, and stone fruit. It is also used in postharvest storage and as treatment in seed preplanting, frequently in combination with other fungicides. In some areas, it has been used to combat Dutch Elm disease.

7.16 First aid: Speed in removing material from eyes and skin is of extreme importance. Eyes: Eye contact can cause dangerous amounts of these chemicals to be quickly absorbed through the mucous membrane into the bloodstream. Immediately and gently flush eyes with plenty of warm or cold water (NO hot water) for at least 15 minutes, occasionally lifting the upper and lower eye lids. Get medical aid immediately. Skin: Get medical aid. Dermal contact can cause dangerous amounts of these chemicals to be absorbed into the bloodstream. Wearing the appropriate PPE equipment and respirator for carbamate pesticides, immediately flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Shampoo hair promptly if contaminated; protect eyes. Ingestion: Call poison control. Loosen all clothing. Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious, alert, and able to swallow, rinse mouth and have victim drink 4 to 8 oz of water. Check to see if poison control instructs you to use ipecac syrup, otherwise administer slurry of activated charcoal (2 oz in 8 oz of water). If victim is UNCONSCIO United States OR HAVING CONVULSIONS, do nothing except keep victim warm. In some cases you may be specifically instructed by poison control to induce vomiting by way of 2 tablespoons of syrupof ipecac (adult) washed down with a cup of water. Do NOT give activated charcoal before or with ipecac syrup. Inhalation: Get medical aid. Do not contaminate yourself. Wearing the appropriate PPE equipment and respirator for carbamate pesticides, immediately remove the victim from the contaminated area to fresh air. If the victim is not breathing, administer artificial respiration. Do not use mouth-tomouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. If breathing is difficult, administer oxygen through bag/mask apparatus until medical help arrives. Do not leave victim unattended.

7.17 Metabolic pathway: When the mites are exposed to 14C-carbendazim, the major carbendazim metabolite identified in the bulb mites is 5-hydroxy-2-aminobenzimidazole. Low levels of 2-aminobenzimidazole and 5-hydroxy-2- benzimidazole carbamate are also identified.

7.18 Shipping: UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

7.19 Incompatibilities: Carbamates are incompatible with reducing agents, strong acids, oxidizing acids, peroxides, and bases. Contact with active metals or nitrides cause the release of flammable, and potentially explosive, hydrogen gas.

7.20 Waste Disposal: Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

7.21 Description: Carbendazim is the degradation product and active ingredient of the carbamate fungicide benomyl. Carbendazim (100 μM) disrupts the growth of S. cerevisiae by inhibiting microtubule polymerization. It impairs meiosis and steroidogenesis in an ex vivo rat model of seminiferous tubules and increases prostate weight in rats when administered at a dose of 100 mg/kg but does not affect other testosterone-dependent or estrogen-dependent tissues.

7.22 Uses: Carbendazim is the most widely used active ingredient in the benzimidazole class of fungicides. It is a systemic fungicide with both protective and curative activities against a wide range of fungal diseases, especially caused by most Ascomycetes spp. and some Basidiomycetes and Deuteromycetes spp. in a wide variety of crop and ornamental uses.

7.23 Trade name: ABACOL?; AIMCOZIM; BAS? 3460; BAS? 67054; BATTAL?; BAVISTIN?; BENDAZIM?; CARBATE?; CARBENDAZIME?; CARBENDAZOL?; CARBENDAZOLE?; CARBENDAZYM?; CARBENDOR; CEKUDAZIM?; CORBEL; CTR? 6669; CUSTOS?; DEFENSOR?; DELSENE?; DEROSAL?; E-965?; DERROPRENE?; EQUITDAZIN?; FUNGISOL?; HOE 17411?; LIGNASAN?; IMISOL?; KEMDAZIN?; MERGAL?; PILLARSTIN?; POLYPHASE?; RODAZIM?; STEMPOR?; SUPERCARB, TRITICOL?; TRITICOL?; U-32.104?

7.24 Biochem/physiol Actions: B-cell maturation antigen (BCMA) or tumor necrosis factor receptor superfamily member 17 (TNFRSF17) plays an important role in B cell development, function and regulation. BCMA also has the capability to activate nuclear factor-κB (NF-κB), janus kinase (JNK) and mitogen activated protein kinases (MAPKs). The protein is expressed in certain cancers like glioblastoma, chronic lymphocytic leukemia, Hodgkin lymphoma and multiple myeloma. It has a role in the maintenance of survival of long-lived plasma cells in bone marrow.

7.25 Degradation: Carbendazim (MBC, 1) was stable in acidic and neutral solutions (pH 5-7, DT₅₀≥57 days at 22°C), but decomposed rapidly with a DT₅₀ of 22 days (WHO, 1993b) to yield 2-aminobenzimidazole (2, Watluns, 1976; Zbozinek, 1984) under alkaline conditions (pH 9). An increase in the salinity of the water accelerated the degradation rate of MBC in water (Deshpande and Patil, 1987).
Photolysis of MBC in natural sunlight is not a significant dissipation mechanism in the environment. Significant degradation did not occur either on leaf surfaces exposed to natural sunlight or in unamended dilute aqueous solution. Degradation occurred in solution under natural sunlight if photoinitiators such as riboflavin or acetone were present (Fleeker and Lacy, 1977).

8. Computational chemical data

Molecular Weight: 191.18700g/mol
Molecular Formula: C₉H₉N₃O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 191.069476538
Monoisotopic Mass: 191.069476538
Complexity: 222
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 67
Heavy Atom Count: 14
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzMAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHgAQAAAACAiBFgIz2LbJlACoASRifACCgC2hEqAJmSAwdJmIaKLAmZGUIAhokQJIyCcQAAAAAAAAAAAAACAAAAAAAAAAQAAAAAAAAA==

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