Butylate (herbicide)

Weed control herbicide

Butylate

Names
Preferred IUPAC name

S-Ethyl N,N-bis(2-methylpropyl)carbamothioate

Other names

* Butilate
* Sutan
* S-Ethyl diisobutylthiocarbamate
* S-Ethyl N,N-diisobutylthiocarbamate

Identifiers

CAS Number

* 2008-41-5

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:34594

ChEMBL |

* ChEMBL1873329

ChemSpider |

* 15357 N

ECHA InfoCard | 100.016.289
EC Number |

* 217-916-3

PubChem CID

* 16181

UNII |

* 3U78PG73G7

CompTox Dashboard (EPA)

* DTXSID7023936

InChI

* InChI=1S/C11H23NOS/c1-6-14-11(13)12(7-9(2)3)8-10(4)5/h9-10H,6-8H2,1-5H3

Key: BMTAFVWTTFSTOG-UHFFFAOYSA-N

SMILES

* CCSC(=O)N(CC(C)C)CC(C)C

Properties

Chemical formula

| C11H23NOS
Molar mass | 217.37 g·mol−1
Appearance  | Amber liquid[1]
Odor | Aromatic odor[1]
Density | 940 kg/m3[2]
Melting point | 137.7[2] °C (279.9 °F; 410.8 K)
Boiling point | 292.6 °C (558.7 °F; 565.8 K) [3]

Solubility in water

| 45 mg/L[2]
Vapor pressure | 170 mPa[2]
Hazards
GHS labelling:

Hazard statements

| H312, H332[2]
Flash point | 115 °C (239 °F; 388 K)
Lethal dose or concentration (LD, LC):

LD50 (median dose)

* 3500 mg/kg (rat, oral)
* >4640 mg/kg (birds)[2]

LC50 (median concentration)

| >4.2 mg/L (freshwater fish, 96 hours)[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Butylate or butilate is a widely used thiocarbamate herbicide. As a herbicide, it was introduced in 1962,[2] and it quickly became the fourth most used herbicide in the US, with 28.5 million pounds (12.9 thousand tonnes) used in 1974.[4] Its use has declined significantly, to 15 million pounds (6.8 thousand tonnes) in 1991 to 950 thousand pounds (430 tonnes) by 1998. It is used on corn (field, sweet, and popcorn), to control grassy and broadleaf weeds and nutsedge.[5]

## Application

[edit]

Butylate is applied as an emulsifiable concentrate of 85% active ingredient and is incorporated into the soil, being applied preplant, at plant, postplant, or after harvest. Its maxmimum application rate is 6.3 lb/acre (7.1 kg/Ha), which is much higher than many other herbicides. Soil incorporation is necessary due to the high volatility.[5] Granular and encapsulated forms are also used. Butylate is often used in combination with atrazine and cyanazine.[6]

There is no residential application of butylate; its use is only on feed-crop.[5]

Butylate can interact with other thiocarbamate herbicides in plants, such as with carbofuran, which reduces synergistically the root and shoot growth of barley, as carbofuran slows the plant's metabolism of butylate, thus letting it accumulate. The effect is not seen on corn, where both carbamates compete for the same mode of uptake.[7]

## Health

[edit]

Butylate is not toxic, not carcinogenic, not teratogenic and not mutagenic.[6] Rat trials show acute neurotoxic effects at the lowest observed adverse effects level (LOAEL) of 2,000 mg/kg/day, leading to a no observed adverse effects level (NOAEL) of 600 milligrams/kilogram/day being established for the general population. At 400 mg/kg/day, rat offspring development was affected, showing decreased fetal weights and increased incidences of misaligned sterebrae,[5] although no developmental effect at any dose is noted in rabbits.[6]

The EPA estimates human food exposure was under 0.3% of the permissible dose for all population subgroups, and so dietary risk of butylate is not a concern.[5][6] Butylate is metabolised rapidly, so there are no residues expected in meat, milk, poultry or eggs, and no intact residues are found in harvested corn.[6]

The EPA requires that pesticide applicators wear, among other items, pants.[6]

## Environmental

[edit]

Butylate has high volatility, with a vapor pressure of 170 mPa, so it may drift outside of target areas.[2] Butylate is mobile to slightly mobile in soil. Ground water contamination is not expected.[5] Technical butylate is highly toxic to freshwater fish, and non-toxic to birds and mammals. Surface water runoff may occur after rain.[6]

## References

[edit]

1. ^ a b "Butylate". pubchem.ncbi.nlm.nih.gov.
2. ^ a b c d e f g h i Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
3. ^ "Butylate | C11H23NOS". www.chemspider.com.
4. ^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
5. ^ a b c d e f "Butylate | Pesticides | US EPA". archive.epa.gov. Retrieved 18 November 2024.
6. ^ a b c d e f g "Butylate: Reregistration Eligibility Decision (RED) Fact Sheet - US EPA ARCHIVE". archive.epa.gov. EPA. Retrieved 18 November 2024.
7. ^ Hamill, Allan S.; Penner, Donald (1973). "Butylate and Carbofuran Interaction in Barley and Corn". Weed Science. 21 (4): 339–342\. ISSN 0043-1745.

## Links

[edit]

* Butylate (herbicide) in the Pesticide Properties DataBase (PPDB)

* v
* t
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Pest control: herbicides

Anilides/anilines|

* acetochlor
* alachlor
* asulam
* benfluralin
* butachlor
* diethatyl
* diflufenican
* dimethenamid
* flamprop
* metazachlor
* metolachlor
* oryzalin
* pendimethalin
* pretilachlor
* propachlor
* propanil
* trifluralin

Aromatic acids|

* aminopyralid
* chloramben
* clopyralid
* dicamba
* picloram
* pyrithiobac
* quinclorac
* quinmerac

Arsenicals|

* cacodylic acid
* copper arsenate
* DSMA
* MSMA

HPPD inhbitors|

* flurochloridone
* isoxaflutole
* leptospermone
* mesotrione
* nitisinone
* sethoxydim
* sulcotrione

Nitriles|

* DCBN
* bromoxynil
* ioxynil

Organophosphorus|

* bensulide
* bialaphos
* ethephon
* fosamine
* glufosinate
* glyphosate
* piperophos

Phenoxy|

| Auxins|

* 2,4-D
* 2,4-DB
* dichlorprop
* fenoprop
* MCPA
* MCPB
* mecoprop
* 2,4,5-T

|

ACCase inhibitors|

| FOP herbicides|

* chlorazifop
* cyhalofop
* diclofop
* fenoxaprop
* fluazifop
* haloxyfop
* quizalofop

|

DIM herbicides|

* sethoxydim
* clethodim

Protox inhibitors|

| Nitrophenyl ethers|

* acifluorfen
* aclonifen
* bifenox
* fluorodifen
* fomesafen
* lactofen
* nitrofen
* oxyfluorfen

|

Pyrimidinediones|

* butafenacil
* saflufenacil

Triazolinones|

* carfentrazone
* sulfentrazone

Pyridines|

* dithiopyr
* fluroxypyr
* imazapyr
* thiazopyr
* triclopyr

Quaternary|

| Photosystem I inhibitors|

* cyperquat
* diquat
* paraquat

|

Thiocarbamates|

* Benthiocarb
* Butylate
* S-Ethyl dipropylthiocarbamate
* prosulfocarb

Triazines|

| cellulose biosynthesis inhibitors|

* indaziflam

|

Photosystem II inhibitors|

* ametryn
* atrazine
* cyanazine
* hexazinone
* metamitron
* metribuzin
* prometon
* prometryn
* propazine
* simazine
* simetryn
* terbuthylazine
* terbutryn

Ureas|

| Photosystem II inhibitors|

* chlortoluron
* DCMU
* difenoxuron
* isoproturon
* linuron
* monuron
* monolinuron
* tebuthiuron

|

ALS inhibitors|

* chlorsulfuron
* flazasulfuron
* metsulfuron-methyl
* sulfometuron methyl
* tribenuron

Others|

* 3-AT
* aminocyclopyrachlor
* Bentazon
* clomazone
* dinoseb
* dinoterb
* juglone
* methazole
* metam sodium
* pyribenzoxim

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H312]: H312: Harmful in contact with skin
*[H332]: H332: Harmful if inhaled
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template