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AMINOPYRALID - The Dow Chemical Company

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www.dowagro.com/usag 1-800-258-3033<br />

®Trademark of <strong>Dow</strong> AgroSciences LLC<br />

V45-313-001 (01/05) BOD<br />

010-50433<br />

<strong>AMINOPYRALID</strong><br />

TECHNICAL BULLETIN<br />

<strong>AMINOPYRALID</strong> IS NOT YET REGISTERED WITH THE U.S. EPA. FEDERAL REGISTRATION IS PENDING.<br />

THIS BULLETIN IS INTENDED TO PROVIDE TECHNICAL INFORMATION ONLY AND IS NOT AN OFFER FOR SALE OF PRODUCT.


Overview<br />

Aminopyralid (DE-750) is a new pyridine carboxylic acid herbicide intended for use in rangeland,<br />

permanent grass pastures, industrial vegetation management areas (including rights-of-way for roads,<br />

railroads and electric utility lines), natural areas (wildlife management areas, natural recreation areas,<br />

campgrounds, trailheads and trails), grazed areas in and around these sites, wheat, barley, sorghum<br />

and oil palm and rubber plantations. It is a new <strong>Dow</strong> AgroSciences compound designed and developed<br />

specifically for the control of noxious and invasive weed species in rangeland, pastures and industrial<br />

vegetation management sites. Aminopyralid is a new generation active ingredient that is effective at<br />

very low rates as compared to currently registered herbicides with the same mode of action, including<br />

2,4-D, clopyralid, triclopyr, picloram and dicamba. Aminopyralid is a broadleaf weed herbicide that<br />

provides systemic, postemergence control of noxious and invasive annual, biennial and perennial weed<br />

species, agronomically important weeds and certain semi-woody plants. Aminopyralid can provide<br />

residual control, thus reducing the need for re-treatment, depending on the rate applied and the target weeds.<br />

Once registered and commercialized, aminopyralid will be offered as a stand-alone treatment and in<br />

premixes with 2,4-D, fluroxypyr and triclopyr for use in rangeland, pastures, rights-of-way and natural<br />

areas. <strong>Dow</strong> AgroSciences intends to register aminopyralid globally. Applied as a stand-alone treatment,<br />

aminopyralid will control important invasive pasture weeds, including Acroptilon repens, Carduus<br />

nutans, Centaurea maculosa, Centaurea solstitialis, Cirsium arvense, Solanum viarum and Senecio<br />

jacobaea. Aminopyralid premixes, with other herbicides, will provide control of a broad spectrum of<br />

broadleaf weeds, including species in the genera Vernonia, Rumex, Urtica, Sida, Solidago, Vervain,<br />

Acacia and Mimosa.<br />

In wheat, aminopyralid can be applied for selective, postemergence control of key broadleaf weeds,<br />

including Polygonum convolvulus, Papaver rhoeas, Polygonum aviculare, Silybum marianum and<br />

Chrysanthemum segetum. Additional cereals concepts utilize fluroxypyr and florasulam as premix partners<br />

and metsulfuron in a co-pack. Product concepts for aminopyralid in wheat are being developed for use<br />

in Argentina, Australia, the United States, Europe, the middle East and Africa.<br />

Cirsium arvense Carduus nutans<br />

Additional product concepts being developed are for the use of aminopyralid + glyphosate in oil palm<br />

and rubber plantations; and aminopyralid + fluroxypyr for use in sorghum. Aminopyralid is selective<br />

in oilseed rape in Europe in concepts that will allow excellent control of a number of key dicot weeds,<br />

including species of Cirsium, Matricaria, Polygonum, Papaver, Galium and Geranium. Evaluations of the<br />

potential to develop aminopyralid alone or in co-formulation with other active ingredients in oilseed<br />

rape are ongoing.<br />

Noteworthy Features<br />

Aminopyralid was accepted for evaluation under the EPA’s Reduced Risk Pesticide program in October<br />

2004. Aminopyralid was accepted into this program based upon a combination of unique and improved<br />

features for the control of invasive weeds in rangeland, pastures, and non-cropland, compared to<br />

currently registered products. EPA’s decision to evaluate aminopyralid as part of its Reduced Risk initiative<br />

was based on data and risk assessments presented for toxicological, ecotoxicological and environmental<br />

fate effects.<br />

Aminopyralid applied alone and with other herbicides will provide the following attributes:<br />

Matricaria inodora<br />

1. Equivalent or superior postemergence and residual control of a broad spectrum of difficult-to-control<br />

noxious and invasive broadleaf or semi-woody plants compared to currently registered herbicides.<br />

2. Reduction in environmental herbicide loading in rangeland and pastures, industrial vegetation<br />

management areas, and natural areas by offering excellent control of many key species at rates<br />

substantially lower than labeled use rates for many currently registered herbicides.<br />

3. Residual weed control activity to reduce the need for re-treatment.<br />

4. An excellent fit into integrated weed management (IWM) programs.<br />

5. Efficacious control in cereals of Polygonum convolvulus, Polygonum aviculare, Papaver rhoeas<br />

(including ALS resistant and 2,4-D tolerant biotypes) and other broadleaf weeds<br />

6. Excellent tolerance and improved, weed free growth of perennial temperate and tropical forage<br />

grass species and grass crops such as wheat, barley and sorghum when used as recommended.<br />

7. A mode of action that provides an alternative to ALS-inhibitor herbicides for ALS herbicide resistant weeds.<br />

2 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 3


<strong>The</strong> Aminopyralid Story<br />

Unmet Needs in Rangeland and Pastures,<br />

Rights-of-Way and Wildlife Management Areas<br />

One of the most serious problems facing landowners and<br />

land managers for rangeland and pastures, rights-of-way<br />

and natural areas is the rapid spread of noxious and<br />

invasive plants. Non-native invasive plants have been<br />

introduced into new habitats without the natural enemies<br />

that limited their reproduction and spread in their native<br />

habitats. <strong>The</strong>se invasive plants are spreading rapidly in<br />

many areas. <strong>The</strong> infestation rate on Federal lands in the<br />

U.S. is now approximately 4,600 acres per day 1 . <strong>The</strong> U.S.<br />

Geological Survey reports that some $20 billion in<br />

damages can be linked to invasive plants. When left<br />

uncontrolled, invasive weed species are a form of biological<br />

pollution and produce many direct and secondary negative<br />

effects. <strong>The</strong>se effects include the creation of plant monocultures that negatively impact endangered<br />

species, crowd out native species that are essential to properly functioning ecosystems, reduce production<br />

of forages used by game and livestock through competition and allelopathy, reduce rangeland carrying<br />

capacity, increase livestock production costs, increase soil erosion, increase rights-of-way maintenance needs<br />

and degrade the aesthetic qualities of desired plant communities.<br />

<strong>Dow</strong> AgroSciences has been a leader in providing effective herbicides for use in rangeland, pastures,<br />

rights-of-way and natural areas for many years. Continuing in this tradition, <strong>Dow</strong> AgroSciences is<br />

developing aminopyralid as a new active ingredient specifically designed for the management of noxious<br />

and invasive species and broad spectrum, broadleaf weed control in rangeland, pastures and rights-of-way.<br />

Aminopyralid is a new generation active ingredient of the pyridine carboxylic acid class that provides an<br />

effective tool for managing these difficult-to-control weeds using reduced application rates. Aminopyralid<br />

fits well into an integrated weed management program due to the low use rate. Overall, aminopyralid<br />

should prove to be a valuable tool in integrated systems approaches to managing rangeland, pasture,<br />

rights-of-way, non-cropland and natural area vegetation complexes.<br />

1 Asher and Harman, International J. of Wilderness 1(2) 1995. 35-37<br />

Formulations<br />

<strong>The</strong>re are currently a wide range of aminopyralid formulation concepts in development to meet widely<br />

varying user needs in different geographic areas and crops around the world. Each of these concepts is<br />

designed to address specific weed management objectives. In some situations, aminopyralid will be<br />

sold in products in which it is a single active ingredient. To meet other specific needs, aminopyralid will<br />

be offered in mixtures or combinations with additional active ingredients.<br />

Registrations<br />

<strong>Dow</strong> AgroSciences will seek to register aminopyralid for use in more than 50 countries in North<br />

America, Central and South America, Europe, Asia, Australia and New Zealand. Initial aminopyralid<br />

registrations are anticipated from 2005 through 2008.<br />

4 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 5


Weed Control<br />

Vernonia baldwinii Solanum carolinense Mimosa pudica<br />

Aminopyralid products will provide selective, broad-spectrum control of annual, biennial and perennial<br />

broadleaf and semi-woody plants. Products are being developed for use in rangeland, pastures, industrial<br />

vegetation management areas, cereals, oil palm and rubber plantations.<br />

I. Range and Pasture, Rights-of-way and Natural Areas<br />

Aminopyralid controls a number of invasive plants and noxious weeds, woody and semi-woody plants<br />

including most of the species from the genera Acacia and Mimosa. Some woody and semi-woody<br />

species are treated on an individual plant basis. Aminopyralid will be recommended alone and or<br />

in pre-mixes with other herbicides.<br />

Long-term weed control is most effective where grass and other desirable vegetation form competitive<br />

stands after the aminopyralid application. <strong>The</strong> benefits of weed control achieved with aminopyralid may<br />

be optimized and extended when integrated with other vegetation management practices (i.e., prescribed<br />

fire, grazing management, fertilization, planting improved temperate and tropical grass and legume<br />

forages, mechanical controls, biological controls, etc.) that promote recovery of desirable vegetation<br />

and increase forage production.<br />

<strong>The</strong> following tables provide a listing of key economic weed species that are susceptible to aminopyralid<br />

and its mixtures with 2,4-D, fluroxypyr or triclopyr, when applied as a broadcast (Table 1) or directed<br />

spray (Table 2) in rangeland, pastures, rights-of-way, other non-cropland and certain crops. Examples<br />

of these weeds include Daucus carota, Solidago sp., Rumex sp., Vernonia sp., Vervain sp., Lespedeza sp.,<br />

Ranunculus sp., Urtica sp., Taraxacum officinale, Symphoriocarpus occidentalis, Capsella bursa-pastoris<br />

and Lantana camara.<br />

Cirsium vulgare Lantana camara Sida rhombifolia<br />

Table 1. List of weeds controlled by aminopyralid and its mixtures in R&P as g ae/ha (broadcast)*<br />

Bayer Species Name Bayer Species Name Bayer Species Name Bayer Species Name<br />

Code Code Code Code<br />

Aminopyralid Aminopyralid + 2,4-D Aminopyralid + Fluroxypyr Aminopyralid + Triclopyr<br />

6 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 7<br />

CENRE**<br />

AMASP<br />

AMBEL<br />

AMBPS<br />

AMBTR<br />

ARTAB<br />

CRUAC<br />

CRUNU<br />

CENDI**<br />

CENMA**<br />

CENSO<br />

CHYLE<br />

CIRAR<br />

CIRVU<br />

LACSE<br />

LAMAN<br />

MATIN<br />

RANBU<br />

RUMAC<br />

RUMCR<br />

RUMOB<br />

SENJA<br />

SOLVI<br />

VEEAT<br />

VENBA<br />

XANST<br />

Acroptilon repens<br />

Amaranthus spinosus<br />

Ambrosia artemisiifolia<br />

Ambrosia psilostachya<br />

Ambrosia trifida<br />

Artemisia absinthium<br />

Carduus acanthoides<br />

Carduus nutans<br />

Centaurea diffusa<br />

Centaurea maculosa<br />

Centaurea solstitialis<br />

Chrysanthemum leucantheum<br />

Cirsium arvense<br />

Cirsium vulgare<br />

Lactuca serriola<br />

Lamium amplexicaule<br />

Matricaria inodora<br />

Ranunculus bulbosus<br />

Rumex acetosa<br />

Rumex crispus<br />

Rumex obtusifolius<br />

Senecio jacobaea<br />

Solanum viarum<br />

Verbesina alternafolia<br />

Vernonia baldwinii<br />

Xanthium strumarium<br />

AMASP<br />

AMBEL<br />

AMBPS<br />

AMBPS<br />

ARTAB<br />

CENDI<br />

CENMA**<br />

CHYUV<br />

CHEAM<br />

CICIN<br />

CIRVU<br />

CVNCP<br />

DAUCA<br />

DEMIL<br />

EUPSQ<br />

GUEDR<br />

HENAM<br />

HPYSU<br />

IVAAN<br />

IVAXA<br />

SIDGZ<br />

SIDRH<br />

SIDSN<br />

SOLCA<br />

SOOMS<br />

SYPOC<br />

VEBST<br />

VENAL<br />

Amaranthus spinosus<br />

Ambrosia artemisiifolia<br />

Ambrosia psilostachya<br />

Ambrosia spilostachya<br />

Artemisia absinthium<br />

Centaurea diffusa<br />

Centaurea maculosa<br />

Tanacetum vulgare<br />

Chenopodium ambrosioides<br />

Cichorium intybus<br />

Cirsium vulgare<br />

Croton capitatus<br />

Daucus carota<br />

Desmanthus illinoensis<br />

Eupatorium squalidum<br />

Gutierrezia dracunculoides<br />

Helenium amarum<br />

Hyptis suaveolens<br />

Iva annua<br />

Iva xanthifolia<br />

Sida glaziovii<br />

Sida rhombifolia<br />

Sida santaremnensis<br />

Solanum carolinense<br />

Solidago missouriensis<br />

Symphoricarpos occidentalis<br />

Verbena stricta<br />

Vernonia altissima<br />

CAPBP<br />

CHEAL<br />

CIRAR<br />

CIRVU<br />

EUPSQ<br />

HERSP<br />

IVAXA<br />

MATCH<br />

POLCO<br />

RANRE<br />

RANSA<br />

RUMAC<br />

RUMCR<br />

RUMOB<br />

CASOB<br />

SIDGZ<br />

SIDRH<br />

SIDSN<br />

STEME<br />

TAROF<br />

URTDI<br />

VENPO<br />

VENWE<br />

Capsella bursa-pastoris<br />

Chenopodium album<br />

Cirsium arvense<br />

Cirsium vulgare<br />

Eupatorium squalidum<br />

Heracleum sphondylium<br />

Iva xanthifolia<br />

Matricaria chamomilla<br />

Polygonum convolvulus<br />

Ranunculus repens<br />

Ranunculus sardous<br />

Rumex acetosa<br />

Rumex crispus<br />

Rumex obtusifolius<br />

Senna obtusifolia<br />

Sida glaziovii<br />

Sida rhombifolia<br />

Sida santaremnensis<br />

Stellaria media<br />

Taraxacum officianale<br />

Urtica dioica<br />

Vernonia polyanthes<br />

Vernonia westiniana<br />

Bayer Species Name Bayer Species Name Bayer Species Name<br />

Code Code Code<br />

Aminopyralid Aminopyralid + 2,4-D Aminopyralid + Fluroxypyr<br />

AROCA<br />

CRUNU<br />

CIRVU<br />

RUMOB<br />

SENJA<br />

SLYMA<br />

Arctotheca calendula<br />

Carduus nutans<br />

Cirsium vulgare<br />

Rumex obtusifolius<br />

Senecio jacobaea<br />

Silybum marianum<br />

ACACO<br />

ACAFA<br />

ACAPT<br />

ASCCU<br />

BATRE<br />

BOICA<br />

LIPNO<br />

MEOPA<br />

MIMAL<br />

MIMPI<br />

MIMPU<br />

CASTO<br />

SIDAC<br />

SIDRH<br />

SOLJA<br />

WSSAM<br />

Acacia cornigera<br />

Acacia farnesiana<br />

Acacia pennatula<br />

Asclepias curassavica<br />

Baltimora recta<br />

Borreria capitata<br />

Lippia nodiflora<br />

Melochia parviflora<br />

Mimosa albida<br />

Mimosa pigra<br />

Mimosa pudica<br />

Senna obtusifolia<br />

Sida acuta<br />

Sida rhombifolia<br />

Solanum jazminoide<br />

Wissadula amplissima<br />

ACADE<br />

ACAHA<br />

ACALE<br />

ACASC<br />

EUPAD<br />

EUPRI<br />

LANCA<br />

LANMV<br />

MACCO<br />

MALPA<br />

RUMSS<br />

Acacia decora<br />

Acacia harpophylla<br />

Acacia leiocalyx<br />

Acacia salicina<br />

Ageratina adenophora<br />

Ageratina riparia<br />

Lantana camara<br />

Lantana montevidensis<br />

Maclura chinensis<br />

Malva parviflora<br />

Rumex sp.<br />

CAPBP<br />

CHEAL<br />

CIRAR<br />

CIRVU<br />

HERSP<br />

MATCH<br />

RUMCR<br />

RUMOB<br />

TAROF<br />

URTDI<br />

Capsella bursa-pastoris<br />

Chenopodium album<br />

Cirsium arvense<br />

Cirsium vulgare<br />

Heracleum sphondylium<br />

Matricaria chamomilla<br />

Rumex crispus<br />

Rumex obtusifolius<br />

Taraxacum officinale<br />

Urtica dioica<br />

* <strong>Dow</strong> AgroSciences research<br />

** Rating base on control achieved one year after application of aminopyralid.<br />

For specific geographic and crop conditions, end-users should consult their local product labels and/or contact a <strong>Dow</strong> AgroSciences representative.<br />

Table 2. List of weeds controlled by aminopyralid and its mixtures in R&P as g ae/100L (directed)<br />

For specific geographic and crop conditions, end-users should consult their local product labels and/or contact a <strong>Dow</strong> AgroSciences representative.


II. Cereals – All Areas<br />

In wheat, aminopyralid has shown excellent postemergence<br />

control, as well as residual activity on key broadleaf weeds,<br />

including Polygonum convolvulus, Papaver rhoeas (including<br />

ALS resistant and 2,4-D tolerant biotypes), Polygonum aviculare,<br />

Silybum marianum and Chrysanthemum segetum. <strong>Dow</strong><br />

AgroSciences will recommend aminopyralid + fluroxypyr in<br />

Australia and in the United States for the control of<br />

Polygonum convolvulus, Polygonum aviculare, Polygonum<br />

vaccinifolium and Kochia scoparia. In Europe, Asia and Africa,<br />

<strong>Dow</strong> AgroSciences will seek registration of aminopyralid in<br />

mixtures designed for specific weed management needs.<br />

Use rates for aminopyralid in wheat will vary from 4 g ae/ha<br />

to 10 g ae/ha. Table 3 lists cereal weeds that are susceptible<br />

to aminopyralid alone and in mixtures.<br />

Table 3. List of weeds controlled by aminopyralid and its mixtures in cereals as g ae/ha (broadcast)<br />

Bayer Species Name Bayer Species Name Bayer Species Name Bayer Species Name<br />

Code Code Code Code<br />

Aminopyralid Aminopyralid + Fluroxypyr Aminopyralid + Florasulam Aminopyralid + Metsulfuron<br />

AROCA<br />

CHYSE<br />

CIEAR<br />

EMEAU<br />

LACSE<br />

MATSS<br />

PAPRH<br />

PIBSA<br />

POLAV<br />

POLCO<br />

SLYMA<br />

VICFX<br />

VICSA<br />

Arctotheca calendula<br />

Chrysentemum segetum<br />

Cicer arietinum*<br />

Emex australis<br />

Lactuca serriola<br />

Matricaria spp.<br />

Papaver rhoeas<br />

Pisum sativum*<br />

Polygonum aviculare<br />

Polygonum convolvulus<br />

Silybum marianum<br />

Vicia faba*<br />

Vicia sativa*<br />

KCHSC<br />

LACSE<br />

PAPRH<br />

POLCO<br />

Kochia scoparia<br />

Lactuca serriola<br />

Papaver rhoeas<br />

Polygonum convolvulus<br />

ANTAR<br />

BIFRA<br />

CIRAR<br />

GALAP<br />

MATSS<br />

PAPRH<br />

SINAR<br />

STEME<br />

Anthemis arvensis<br />

Bifora radians<br />

Cirsium arvense<br />

Galium aparine<br />

Matricaria spp.<br />

Papaver rhoeas<br />

Sinapis arvensis<br />

Stellaria media<br />

Triticum aestivum<br />

CENSO<br />

CHEAL<br />

LAMAM<br />

LYCAR<br />

POLAV<br />

POLCO<br />

RAPRA<br />

RASRU<br />

STEME<br />

Centaurea solstitialis<br />

Chenopodium album<br />

Lamium amplexicaule<br />

Lycopsis arvensis<br />

Polygonum aviculare<br />

Polygonum convolvulus<br />

Raphanus raphanistrum<br />

Rapistrum rugosum<br />

Stellaria media<br />

* volunteer plants<br />

For specific geographic and crop conditions, end-users should consult their local product labels and/or contact a <strong>Dow</strong> AgroSciences representative.<br />

III. Oil Palm and Rubber Plantations – Indonesia and Malaysia<br />

<strong>Dow</strong> AgroSciences is developing a premixture of aminopyralid + glyphosate for use in oil palm and rubber<br />

plantations as a postemergence treatment applied around the base of the trees for broad spectrum<br />

foliar control of key broadleaf and grass weeds including Ageratum conyzoides, Asystasia intrusa,<br />

Hedyotis verticillata, Mikania cordata and Paspalum conjugatum.<br />

Mode of Action<br />

Silybum marianum Polygonum convolvulus Polygonum aviculare<br />

Hedyotis verticillata Ageratum conizoides<br />

Plant growth is a complex process that is controlled, in part, by a variety of plant growth regulators,<br />

including auxin compounds. To ensure proper growth, plants produce very controlled amounts of these<br />

materials. Auxins bind to specific cell surface receptor proteins, turning on and off vital plant processes.<br />

Aminopyralid is a herbicide possessing auxin-like qualities. Aminopyralid moves systemically throughout<br />

the plant and deregulates plant growth metabolic pathways affecting the growth process of the plant.<br />

This disruption of plant growth processes, by binding of aminopyralid at receptor sites normally used<br />

by the plant’s natural growth hormones, results in control and death of susceptible plant species.<br />

8 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 9


Absorption/Translocation<br />

Aminopyralid is a systemic, phloem and xylem mobile herbicide that is rapidly absorbed by the leaves<br />

and roots. <strong>The</strong> compound translocates throughout the plant and accumulates in the meristematic tissue,<br />

resulting in uneven cell division and growth.<br />

Herbicidal Activity<br />

Symptoms are typical of those for the auxinic mode of action. Within hours or days of application<br />

depending on the weed species, aminopyralid causes symptoms such as thickened, curved and twisted<br />

stems and leaves, cupping and crinkling of leaves, stem cracking, narrow leaves with callus tissue,<br />

hardened growth on stems, enlarged roots and proliferated growth. Most annual susceptible weeds are<br />

controlled within 4 to 8 weeks after application. Complete kill of main stems and the root systems of<br />

woody and semi-woody plants may require 2 or more months after application. Plant growth will stop<br />

within 24-48 hours after treatment.<br />

Crop Tolerance<br />

Aminopyralid offers a high level of tolerance on a wide range of temperate and tropical forage grasses<br />

and on small grain cereals. More than 20 different forage grasses evaluated in field trials from 1999-2004,<br />

with aminopyralid applied at rates up to 2 times the maximum use rate, demonstrated tolerance to<br />

aminopyralid. <strong>The</strong> grasses evaluated included Agropyron sp., Andropogon gerardii, Andropogon<br />

saccharoides, Andropogon scoparius, Bouteloua curtipendula, Bouteloua gracilis, Brachiaria bryzantha,<br />

Brachiaria decumbens, Bromus inermis, Buchloe dactyloides, Cynodon dactylon, Cynodon nlemfuensis,<br />

Cynodon plectostachyus, Dactylis glomerata, Digitaria decumbens, Eragrostis ciliaris, Festuca sp., Lolium<br />

sp., Panicum maximum, Panicum virgatum, Paspalum notatum, Phleum pratense, Poa sp. and<br />

Sorghastrum nutans.<br />

Aminopyralid may be applied to small grain cereals from the 3-leaf crop growth stage up to the early<br />

joint stage. Field trial results confirm that aminopyralid offers crop selectivity that is equal or superior<br />

to that of standards on wheat, durum wheat, barley, rye and triticale.<br />

Crop Rotation<br />

Rangeland or permanent pasture areas treated with aminopyralid should generally not be rotated to broadleaf<br />

crops including cotton, soybeans, alfalfa, field peas, lentils and other leguminous crops within the same year<br />

of application. Exceptions might occur in tropical/subtropical regions with hot and humid conditions.<br />

Aminopyralid is primarily dissipated in the soil by aerobic microbial degradation and the rate of breakdown<br />

is dependent upon several factors including soil moisture and soil temperature. Specific local guidelines for<br />

planting of rotational crops will be contained on the label. In general, grass crops will be more tolerant as<br />

rotational crops. Rotational crop recommendations for broadleaf crops will vary among species.<br />

Resistance Management<br />

Aminopyralid has an auxinic growth regulator mode of action. Other growth regulator herbicides used<br />

on rangeland and pastures, rights-of-way and other non-cropland areas, natural areas and in cereals,<br />

include 2,4-D, clopyralid, dicamba, picloram and triclopyr. Despite extensive use, herbicides with this mode<br />

of action have demonstrated a low risk of resistance development compared to other herbicide<br />

mode of action classifications such as ALS-inhibitor herbicides, photosystem II inhibitor herbicides<br />

and ACCase-inhibitor herbicides.<br />

<strong>The</strong> International Survey of Resistant Weeds lists only six weed species in the United States and 24 species<br />

worldwide with resistance to the growth regulator mode of action. <strong>The</strong> risk of resistance development is<br />

less on rangeland, pasture and natural areas because herbicide applications are not typically made every<br />

year, thus slowing the increase in resistant genotypes in weed populations. Because of the low resistance<br />

risk, aminopyralid will be a useful herbicide tool to rotate with ALS-inhibitor herbicides and urea herbicides<br />

in range and pastures, non-cropland areas and natural areas.<br />

Worldwide, there currently are 82 weed species with confirmed ALS-inhibitor resistance and 20 with urea<br />

herbicide resistance. Many of these weed biotypes are encountered in rangeland, pastures, rights-of-way<br />

and cereals including Kochia scoparia, Salsola iberica, Papaver rhoeas, Ambrosia sp., Lactuca serriola,<br />

Helianthus annuus, Sinapis arvensis and Amaranthus sp.<br />

Chlorsufuron and sulfometuron are ALS-inhibiting herbicides that have been used repeatedly and extensively<br />

on rights-of-way. Metsulfuron, another ALS-inhibiting herbicide, has been used repeatedly and extensively<br />

on rights-of-way, rangeland and pastures. Triasulfuron, chlorsulfuron, metsulfuron, thifensulfuron and tribenuron<br />

are ALS-inhibiting herbicides that have been used repeatedly and extensively on wheat.<br />

<strong>The</strong>re are only a limited number of herbicide modes-of-action available for rangeland, pasture and<br />

non-cropland areas. <strong>The</strong> existence of multiple known examples of ALS-inhibitor resistant weeds in these<br />

sites and in wheat, confirm the need for a sound weed resistance management strategy. Aminopyralid has<br />

a growth regulator mode of action and will control ALS-inhibitor herbicide and urea herbicide resistant<br />

biotypes for species within the aminopyralid weed spectrum.<br />

10 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 11


Description of Chemistry<br />

<strong>Chemical</strong> Name (IUPAC) 4-amino-3,6-dichloropyridine-2-carboxylic acid<br />

<strong>Chemical</strong> Name (CAS) 2-pyridinecarboxylic acid, 4-amino-3,6-dichloro-<br />

Common Name Aminopyralid (ISO proposed)<br />

Code Names DE-750, XDE-750, XR-750<br />

<strong>Chemical</strong> Class Pyridine carboxylic acid<br />

CAS Registry No. 150114-71-9<br />

Empirical formula C 6 H 4 Cl 2 N 2 O 2<br />

Structural formula<br />

Molecular Weight 207.026 g/mole<br />

Relative Density 1.72 at 20°C<br />

Appearance Off-white, odorless powder<br />

Melting Point 163.5°C<br />

Boiling Point Decomposes upon melting<br />

Vapor pressure At 20°C, 7.14e-11 mmHg<br />

Octanol/Water Partition Unbuffered water = 0.201<br />

Coefficient (log K ow ) at 19°C pH 5 = -1.76<br />

pH 7 = -2.87<br />

pH 9 = -2.96<br />

Dissociation Constant (pK a ) 2.56<br />

Hydrolytic Stability (DT 50 ) Stable<br />

Aqueous Photostability (DT 50 ) 0.6 Days<br />

Soil Photolysis (DT 50 ) 61 Days<br />

Solubility in water 2.48<br />

(g/L @ 18°C)<br />

Solvent solubility<br />

(g/L @ 20°C)<br />

Buffered water pH = 5 212 g/L<br />

Buffered water pH = 7 205 g/L<br />

Buffered water pH = 9 203 g/L<br />

Methanol 52 g/L<br />

Acetone 29 g/L<br />

Heptane Insoluble (< 10 µg/L)<br />

12 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 13


Mammalian Toxicity<br />

I. Short-Term (Acute) Toxicity<br />

Based on data generated for, or on behalf of <strong>Dow</strong> AgroSciences, the acute mammalian toxicity of<br />

aminopyralid is considered low for both technical and end-use formulations. <strong>The</strong> acute oral LD 50 and<br />

dermal LD 50 in rats were greater than 5000 mg/kg, respectively, while the acute inhalation LC 50 was<br />

greater than 5.5 mg/L. Dermal irritation was negative for the aminopyralid technical. Eye irritation ranged from<br />

a slight, transient irritation for formulated aminopyralid to irritating for aminopyralid technical. Aminopyralid<br />

was not a skin sensitizer. A summary of acute toxicology data for aminopyralid is provided below:<br />

Test Species Toxicity Parameters<br />

Acute Oral (technical ai) Rat LD 50 > 5000 mg/kg<br />

Acute Oral (GF-871, Rat LD 50 > 5000 mg/kg<br />

240 g ae/L formulation)<br />

Acute Dermal (technical ai) Rat LD 50 > 5000 mg/kg<br />

Acute Dermal (GF-871, Rat LD 50 > 5000 mg/kg<br />

240 g ae/L formulation)<br />

Acute Inhalation (technical ai) Rat LC 50 male > 5.50 mg/L<br />

Acute Inhalation (GF-871, Rat LC 50 male > 5.79 mg/L<br />

240 g ae/L formulation)<br />

Dermal irritation (technical ai) Rabbit Negative<br />

Dermal irritation (GF-871, Rabbit Slight irritation<br />

240 g ae/L formulation)<br />

Eye Irritation (technical ai) Rabbit Irritating<br />

Eye Irritation (GF-871, Rabbit Slight irritation,<br />

240 g ae/L formulation) resolving within 24 hours<br />

Skin sensitization (technical ai) Guinea Pig No sensitization<br />

Skin sensitization (GF-871, Guinea Pig No sensitization<br />

240 g ae/L formulation)<br />

Long-Term (Chronic) Toxicity<br />

<strong>Dow</strong> AgroSciences studies have shown that aminopyralid (technical) was not carcinogenic,<br />

teratogenic, mutagenic, neurotoxic or a reproductive hazard. Aminopyralid was tested<br />

for genotoxicity in both in vitro and in vivo systems. A summary of long-term (chronic)<br />

toxicity data is provided below:<br />

Test Species Toxicity Parameters<br />

2-year chronic feeding Rat Not carcinogenic<br />

NOAEL (mg/kg/day):<br />

Male = 50, Female = 500<br />

Teratogenicity Rat Not teratogenic<br />

NOAEL (mg/kg/day):<br />

Maternal = 1000<br />

Developmental = 1000<br />

Teratogenicity Rabbit Not teratogenic<br />

NOAEL (mg/kg/day):<br />

Maternal = 250<br />

Developmental = 500<br />

Reproductive toxicity Rat No adverse reproductive effects<br />

NOAEL (mg/kg/day):<br />

Parental = 1000<br />

Reproductive = 1000<br />

Acute and chronic neurotoxicity Rat No adverse neurological effects<br />

Mutagenicity Assay (in vitro) Ames test Negative<br />

Mutagenicity Assay (in vitro) CHO/HGPRT Negative<br />

Mutagenicity Assay (in vivo) Mouse micronucleus Negative<br />

NOAEL (mg/kg/day) = 1000<br />

14 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 15


Environmental Toxicology<br />

In <strong>Dow</strong> AgroSciences laboratory testing, aminopyralid has been shown to be practically non-toxic to<br />

birds, fish, honeybees, earthworms and aquatic invertebrates. While aminopyralid is slightly toxic to the<br />

eastern oyster, algae and aquatic vascular plants, the expected environmental concentration resulting<br />

from the use of this material for weed control is orders of magnitude below any level of concern established<br />

for these organisms by EPA.<br />

Study Species Value<br />

Birds<br />

Avian oral Bobwhite Quail LD 50 > 2250 mg ae/kg bw<br />

Avian dietary Bobwhite Quail LD 50 > 5620 mg ae/kg diet<br />

Avian dietary Mallard Duck LD 50 > 5620 mg ae/kg diet<br />

Fish<br />

Acute toxicity Rainbow Trout 96 hr LC 50 > 100 mg ae/L<br />

Acute toxicity Bluegill 96 hr LC 50 > 100 mg ae/L<br />

Acute toxicity Sheepshead Minnow 96 hr LC 50 > 120 mg ae/L<br />

Study Species Value<br />

Aquatic Invertebrates<br />

Acute toxicity Water flea 48 hr EC 50 > 100 mg ae/L<br />

(Daphnia magna)<br />

Acute toxicity Mysid shrimp 96 hr LC 50 > 100 mg ae/L<br />

Acute toxicity Eastern oyster Slightly toxic<br />

48 hr EC 50 > 89 mg ae/L<br />

Growth and Reproduction Water flea NOEC = 100 mg ae/L<br />

(Daphnia magna)<br />

Chronic Toxicity Midge NOEC = 130 mg ae/L<br />

16 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 17<br />

Honey bees<br />

Acute Contact Honeybee 48 hr LD 50 > 100 ug ae/bee<br />

Acute Oral Honeybee 48 hr LD 50 > 120 ug ae/bee<br />

Earthworm<br />

Acute Toxicity Earthworm 14 d LC 50 > 1000 mg ae/kg soil<br />

Algae and Aquatic Plants<br />

Acute Toxicity Freshwater green algae Slightly toxic<br />

72 hr E r C 50 = 30 mg ae/L<br />

Acute Toxicity Freshwater Slightly toxic<br />

blue-green algae 120 hr EC 50 = 27 mg ae/L<br />

Acute Toxicity Saltwater diatom Slightly toxic<br />

72 hr E b C 50 = 77 mg ae/L<br />

Acute Toxicity Freshwater diatom Slightly toxic<br />

96 hr EC 50 = 14 mg ae/L<br />

Acute Toxicity Duckweed Slightly toxic<br />

(Lemna gibba) 14 d EC 50 > 88 mg ae/L


Environmental Fate<br />

Soil<br />

Aerobic microbial degradation is the primary route of breakdown of aminopyralid in soil. <strong>The</strong> rate of<br />

degradation in the field resulted in an average half-life of 34.5 days for 8 North American sites and<br />

25 days for four European sites.<br />

Laboratory experiments yielded an average K oc of 10.8 L/kg, indicating some potential for mobility.<br />

However, field experiments showed limited movement in the soil profile. No degradation metabolites<br />

of concern were produced in any studies.<br />

Water<br />

In water the primary route of degradation of aminopyralid is photolysis. <strong>The</strong> photolysis half-life under standard<br />

conditions is 0.6 days indicating rapid degradation in surface water. <strong>The</strong> material is stable to hydrolysis.<br />

Groundwater contamination potential for aminopyralid is considered to be low because of low use<br />

rates, the moderate field degradation rates and limited mobility observed in field studies. Using this<br />

information as inputs to EPA and European Union simulation models, aminopyralid demonstrated a low<br />

potential for groundwater contamination.<br />

Air<br />

<strong>The</strong> potential for transport of aminopyralid via<br />

volatilization of residues is extremely low, due to its<br />

low vapor pressure and small Henry’s Law constant.<br />

As with any herbicide, susceptible non-target<br />

plants may be injured via physical spray drift.<br />

Spray applications should be made such that<br />

spray drift cannot injure desirable, susceptible<br />

plant species.<br />

Disclaimer<br />

<strong>The</strong> Aminopyralid Technical Bulletin is provided for reference purposes only and is not a substitute for<br />

or an addition to the product label or MSDS. Always read and follow label directions for registered pesticides.<br />

<strong>The</strong> information and any recommendations in this bulletin (“Information”) are presented in good faith;<br />

however, <strong>Dow</strong> AgroSciences LLC makes no warranty as to the completeness or accuracy of the information.<br />

This information is supplied upon the condition that persons receiving it will make their own determinations<br />

as to its suitability for their purposes prior to use and consult with their advisors to ensure compliance<br />

with all federal, state and local regulations. In no event will <strong>Dow</strong> AgroSciences be responsible for damages<br />

of any nature whatsoever resulting from the use of or reliance on this information.<br />

<strong>AMINOPYRALID</strong> IS NOT YET REGISTERED WITH THE U.S. EPA. FEDERAL REGISTRATION IS<br />

PENDING. THIS BULLETIN IS INTENDED TO PROVIDE TECHNICAL INFORMATION ONLY AND<br />

IS NOT AN OFFER FOR SALE OF PRODUCT.<br />

NO REPRESENTATION OR WARRANTIES, EITHER EXPRESSED OR IMPLIED OF MERCHANTABILITY,<br />

FITNESS FOR A PARTICULAR PURPOSE OR OF ANY OTHER NATURE ARE MADE HERUNDER WITH<br />

RESPECT TO THE INFORMATION OR THE PRODUCTS TO WHICH THE INFORMATION REFERS.<br />

Notice to the State of New York: <strong>The</strong> conclusions which are contained with this Technical Bulletin<br />

relating to the toxicological and environmental properties and effects of aminopyralid are based on<br />

research and studies conducted by <strong>Dow</strong> AgroSciences. All such conclusions and findings are considered<br />

to be the opinions of <strong>Dow</strong> AgroSciences.<br />

18 An Introduction to <strong>AMINOPYRALID</strong> An Introduction to <strong>AMINOPYRALID</strong> 19

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