Kixor Herbicide Technical Brochure - Greg Cunningham

BASF Agricultural Products 26 Davis Drive Research Triangle Park, NC 27709 USA +1 919-547-2000 Kixor, Integrity, OpTill, Sharpen and Treevix are trademarks of BASF. ©2009 BASF Corporation. All Rights Reserved. APN-09-01-079-0020

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Kixor™ Herbicide Technical Brochure

10/12/09 2:39 PM

PREFACE This technical brochure provides general information about Kixor™ herbicide – a new active ingredient under development from BASF Crop Protection. Kixor is not currently registered for use in the United States. The registration dossier for Kixor was submitted for tri-lateral review in the United States, Canada and Australia in January 2008.

DISCLAIMER The product discussed in this technical brochure is not registered and is not available for sale. This technical and educational material is provided for informational purposes only and is not intended to promote the sale of the product. Any sale of this product after registration is obtained shall be solely on the basis of approved product labels, and any claims regarding product safety and efficacy shall be addressed solely by the label.

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TABLE OF CONTENTS

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KIXOR HERBICIDE TECHNICAL BROCHURE


INTRODUCTION

Introduction

5

Key Benefits of Kixor™ Herbicide

5

General Characteristics

6

Weeds Controlled

7

Crop Development Targets

8

Application Considerations

8

The Kixor Herbicide Family of Products

9

Integrity™ Herbicide for Corn and Grain Sorghum

10

OpTill™ Herbicide for Soybean, Dry Field Peas and Chickpeas

11

Sharpen™ Herbicide for Burndown

12

Treevix™ Herbicide for Fruit and Nut Trees

13

Mammalian Toxicology

14

Ecotoxicology

14

Environmental Fate

15

Physical and Chemical Properties

15

Kixor is an innovative, new active ingredient under development by BASF and represents a new standard for broadleaf weed control. Kixor is a highly effective herbicide that will be suitable for contact and residual control of broadleaf weeds. Row crop research has shown that Kixor will be able to be applied prior to crop emer gence for burndown of emerged broadleaf weeds in a number of crops and at higher rates in corn and sorghum for season-long residual broadleaf control. Kixor has also shown potential to be used as a directed postemergence treatment in citrus fruit, pome fruit, stone fruit and nut trees, as a sunflower desiccant, as a postharvest burndown treatment, and as a postemergence treatment in fallow cropland.

KEY BENEFITS OF KIXOR HERBICIDE n

A unique chemistry for the herbicide market.

n

Excellent control of all major broadleaf weeds, including glyphosate, ALS and atrazine-resistant biotypes.

n

Broad-spectrum weed control without the need for atrazine.

n

Rapid foliar burndown and residual soil activity.

n

Safe for use in multiple crops and rotational crop systems.

n

Compatible with other herbicides to provide broad-spectrum weed control.

n

Favorable environmental, toxicological and ecotoxicological profile.

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GENERAL CHARACTERISTICS

This list is a general indication of the burndown and residual spectrum demonstrated in testing.

New Chemistry Kixor™ herbicide is the first in the class known as pyrimidinedione in North America. Kixor was designed with a novel side chain (Figure 1). This novel side chain means that Kixor is readily metabolized by tolerant crops, which leads to excellent crop safety. The novel side chain also imparts chemical properties that result in soil bioavailability and foliar activity that enhance weed control.

Figure 1

WEEDS CONTROLLED Common Name Amaranth, Palmer

Scientific Name Amaranthus palmeri

Common Name Morningglory, pitted

Scientific Name Ipomoea lacunosa

Bedstraw, catchweed

Galium aparine

Morningglory, tall

Ipomoea purpurea

Beggarticks, hairy

Bidens pilosa

Mustard, black

Brassica nigra

Beggarweed, Florida

Desmodium tortuosum

Mustard, tumble

Sisymbrium altissimum

Bindweed, field

Convolvulus arvensis

Mustard, wild

Sinapis arvensis

Crop Safety

Buckwheat, wild

Polygonum convolvulus

Nettle, burning

Urtica urens

Lab studies have shown that tolerant crops, like corn, are capable of rapidly metabolizing Kixor (Figure 2) whereas sensitive weeds, like morningglory, cannot (Figure 3).

Canola, volunteer (rapeseed)

Brassica spp.

Nightshade, black

Solanum nigrum

Carpetweed

Mollugo verticillata

Nightshade, cutleaf

Solanum triflorum

Cocklebur, common

Xanthium strumarium

Nightshade, Eastern black

Solanum ptycanthum

Cowcockle

Vaccaria pyramidata

Nightshade, hairy

Solanum saccharoides

Dandelion

Taraxacum officinale

Pennycress, field

Thlaspi arvense

Eveningprimrose, cutleaf

Oenothera laciniata

Pigweed, prostrate

Amaranthus blitoides

Falseflax, smallseed

Camelina microcarpa

Pigweed, redroot

Amaranthus retroflexus

Fleabane, hairy

Conyza bonariensis

Pigweed, smooth

Amaranthus hybridus

Flixweed

Descurainia sophia

Puncturevine

Tribulus terrestris

Groundcherry, cutleaf

Physalis angulata

Purslane, common

Portulaca oleracea

Groundsel, common

Senecio vulgaris

Ragweed, common

Ambrosia artemisiifolia

Horseweed (marestail)

Conyza canadensis

Ragweed, giant

Ambrosia trifida

Knotweed, prostrate

Polygonum aviculare

Sesbania, hemp

Sesbania exaltata

Kochia

Kochia scoparia

Shepherd’s Purse

Capsella bursa-pastoris

Ladysthumb

Polygonum persicaria

Sida, prickly

Sida spinosa

Lambsquarters, common

Chenopodium album

Lambsquarters, narrowleaf

Chenpodium pratericola

Smartweed, Pennsylvania

Polygonum pensylvanicum

Lettuce, prickly

Lactuca serriola

Sowthistle, annual

Sonchus oleraceus

Sowthistle, spiny

Sonchus asper

Sunflower, common

Helianthus annuus

Tansymustard, pinnate

Descurainia pinnata

Corn

Morningglory

Rapid metabolism

No metabolism 100% Kixor 33% Kixor

Figure 2: 4 hours after treatment

Figure 3: 4 hours after treatment

Data provided by Dean Riechers, University of Illinois at Urbana-Champaign

Uptake and Translocation Kixor is readily absorbed by plant roots, shoots and leaves. Once absorbed, Kixor is predominantly translocated via the xylem, with some movement in the phloem.

Mallow, common

Malva neglecta

Mallow, little (cheeseweed)

Malva parviflora

Mallow, Venice

Hibiscus trionum

Marestail (horseweed)

Conyza canadensis

Thistle, Canada

Cirsium arvense

Morningglory, entireleaf

Ipomoea hederacea var. integriuscula

Thistle, Russian

Salsola kali

Velvetleaf

Abutilon theophrasti

Morningglory, ivyleaf

Ipomoea hederacea

Waterhemp

Amaranthus tuberculatus

Morningglory, palmleaf

Ipomoea wrightii

Willowweed

Epilobium adenocaulon

Mode of Action Kixor is a potent inhibitor of chlorophyll biosynthesis resulting in a rapid buildup of reactive oxygen species and lipid peroxidation of the cellular membranes. This results in a rapid loss of membrane integrity leading to cellular leakage, tissue necrosis and, ultimately, plant death.

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CROP DEVELOPMENT TARGETS

THE KIXOR HERBICIDE FAMILY OF PRODUCTS

Kixor™ herbicide has demonstrated the potential for utility in a variety of cropping systems. Crop selectivity is most often based on physical placement and metabolism but will ultimately depend on the crop species, use rate, soil characteristics and application timing. Kixor cannot be applied after crop emergence or injury will occur.

Integrity™ Herbicide Corn, Grain Sorghum

OpTill™ Herbicide Soybean (Midwest), Chickpeas, Dry Field Peas

Treevix™ Herbicide Citrus Fruit, Pome Fruit, Stone Fruit, Nut

Sharpen™ Herbicide Small Grain Cereals, Corn, Cotton, Fallow, Grain Sorghum, Chickpeas, Dry Field Peas, Soybean, Sunflower (desiccation)

Proposed Crop Species Cereals: barley, oat, wheat

Proposed Application Timing PP, PPI, PRE

Chickpeas and Dry Field Peas

PP, PPI, PRE

Corn

PP, PPI, PRE

Cotton Fallow and Post Harvest Grain Sorghum

PP POST PP, PPI, PRE

Soybean

PP, PRE

Sunflower

POST-Desiccant

Fruit and Nut Trees

POST-Directed

Key: PP = Preplant Surface; PPI = Preplant Incorporated; PRE = Preemergence; POST = Postemergence

APPLICATION CONSIDERATIONS Kixor is being developed as a water-based spray alone or, more commonly, in combination with other herbicides for broad-spectrum control. Studies indicate that when Kixor is applied as a contact herbicide to emerged weeds it should be mixed with a suitable adjuvant system. Maximum burndown activity has been achieved with a an adjuvant system including a crop oil concentrate or methylated seed oil plus a spraygrade, ammonium containing fertilizer such as ammonium sulfate. Adjuvant Crop Oil Concentrate or Methylated Seed Oil PLUS Ammonium Sulfate or Urea Ammonium Nitrate

Rate 1 gal/100 gal (1% v/v) 8.5-17 lb/100 gal (1-2% w/v) 1.25-2.5 gal/100 gal (1.25-2.5% v/v)

Ground applications for which water is the carrier should be made with a proposed minimum spray volume of 5 gal/A. Higher spray volumes typically improve spray coverage and control of larger weeds and denser weed populations. Kixor is nonvolatile, but spray drift must be managed to avoid contact with non-target plant foliage.

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INTEGRITY™ HERBICIDE FOR CORN AND GRAIN SORGHUM

OPTILLTM HERBICIDE FOR SOYBEAN, DRY FIELD PEAS AND CHICKPEAS

Integrity is Kixor™ herbicide plus dimethenamid-p formulated as a liquid emulsifiable concentrate (5.57 lb ai/gal). BASF is developing Integrity for use in corn and grain sorghum as a preplant, preplant incorporated or preemergence treatment in all types of tillage. Integrity has been shown to be effective when used as a full-rate, one-pass treatment or as a reduced-rate setup for a POST, in-crop herbicide application.

OpTill is a dry formulation (68% WG) of Kixor™ herbicide plus imazethapyr in development by BASF for burndown and residual weed control when applied preplant through preemergence.

Key Development Targets n

One-pass, season-long broadleaf and grass control

n

Broad-spectrum weed control without the need for atrazine

n

Unique Kixor chemistry

One-Pass Broadleaf Weed Control (7-10 WAT) 2005-2008 BASF Corn Trial Results

C. Cocklebur (19*) Giant Ragweed (13)

n

Residual broadleaf and grass control

Morningglory spp. (9) Sunflower (3) 40

50

60

70 80 % Control

Treatments**

Untreated

Fast, complete burndown

OpTill + glyphosate

Velvetleaf (36) 90

100

Velvetleaf (6) Waterhemp (5)

n Atrazine-based premix

6 WAT Seymour, IL

Grasses† (23)

* Number of trials ** Treatments applied preemergence +/- 3 days of planting

7 WAT University of Wisconsin

n

Lambsquarters (6*)

C. Sunflower (6)

n Integrity

Key Development Targets

Residual Weed Control (3-8 WAT) 2008 University Soybean Trial Results

Morningglory spp. (26)

Integrity

40 Integrity

glyphosate + 2,4-D ester

One-Pass Broadleaf Weed Control (6-8 WAT) 2008 University Sorghum Trial Results

50

Treatments** n OpTill + glyphosate + COC + AMS

60

70 80 % Control

90

100

n 2,4-D ester + glyphosate + NIS + AMS

* Number of trials ** All treatments applied preplant † Includes: annual bluegrass, barnyardgrass, foxtail spp., johnsongrass, large crabgrass, sprangletop spp.

Ann. Grass (6*) C. Sunflower (2) Morningglory spp. (3) 7 WAT Seymour, IL

Untreated

Palmer Amaranth (6) Integrity

Velvetleaf (3) 0

20

Treatments** n Integrity

40 60 % Control

80

100

n Atrazine-based premix

* Number of trials ** Treatments applied preemergence +/- 3 days of planting

6 WAT Richland, IA

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SHARPEN™ HERBICIDE FOR BURNDOWN Sharpen is being developed by BASF for fast, complete burndown of broadleaf weeds. Field and row crop research has shown that Sharpen will provide excellent burndown control when applied either in preplant to preemergence treatments (corn, chickpeas, dry field peas, grain sorghum, small grain cereals and soybean), in preplant treatments (cotton), for sunflower desiccation, or fallow and postharvest treatments.

Untreated

Broadleaf Weed Burndown (1-2 WAT) 2008 University Soybean Trial Results

Dandelion (4*)

Marestail (8)

9 DAT Washington County, NC

Treevix has been designed for directed, postemergence applications in bearing and non-bearing tree crops (citrus fruit, pome fruit, stone fruit and nut trees). BASF and independent research have confirmed its ability to control over 75 broadleaf weeds with excellent tree safety. Treevix will be formulated for easy tank mixing with other herbicides to provide a complete weed control program. Preharvest intervals are being projected at 0 days for citrus, pome fruit and stone fruit trees and 7 days for nut trees.

Untreated Check


Henbit (9)

Sharpen + glyphosate

TREEVIXTM HERBICIDE FOR FRUIT AND NUT TREES

G. Ragweed (3)

n

Fast, complete broadleaf weed control

n

Tree safe and nonvolatile

n

Application timing flexibility

Treevix + glyphosate

Broadleaf Weed Burndown (<3 WAT) 2005-2008 BASF Fruit and Nut Tree Field Trial Results

Shepherd’s Purse (4) 40

50


Treatments**

n

Fast, complete burndown

n Sharpen + glyphosate + COC + AMS

n

Wide range of crops

* Number of trials ** All treatments applied preplant

n

No antagonism with other herbicides

60

70 80 % Control

90

100 Cheeseweed (8*)


13 DAT Kern County, CA

Fleabane (9) Broadleaf Weed Burndown (<2 WAT) 2008 University Cereal Trial Results Marestail (3) Kochia (4*)

20

Lambsquarters (3)

30

Treatments** n Treevix

Prickly Lettuce (2)

n flumioxazin

40

50

60 70 % Control

80

90

100

n oxyfluorfen

* Number of trials ** All treatments + glyphosate + COC + AMS

Russian Thistle (2) Wild Buckwheat (3) 40

50

Treatments** n Sharpen + glyphosate + COC + AMS

60

70 80 % Control

90

100


* Number of trials ** All treatments applied preplant

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MAMMALIAN TOXICOLOGY Acute mammalian toxicology studies indicate Kixor™ herbicide has low toxicity for mammals after ingestion, dermal exposure or inhalation. It is not an eye or skin irritant and does not act as a sensitizer. Results also indicate Kixor is not a selective reproductive or developmental toxicant, and is not neurotoxic or carcinogenic. Kixor is not genotoxic. Mammalian Toxicology Species Rat Rat Rat Rabbit Rabbit Guinea pig

Study Acute oral Acute dermal Acute inhalation Skin irritation Eye irritation Skin sensitization

Active Ingredient Effect Level LD50 > 2000 mg/kg bw LD50 > 2000 mg/kg bw LC50 > 5.5 mg/L Not irritating Slightly irritating Not sensitizing

ECOTOXICOLOGY Ecotoxicological testing indicates low toxicity and no dangerous acute or chronic effects on birds, fish, aquatic invertebrates, sediment-dwelling organisms, earthworms, honey bees or beneficial arthropods. Ecotoxicology Species Study Active Ingredient Effect Level Mallard duck Acute oral LD50 > 2000 mg/kg bw Bobwhite quail Acute oral LD50 > 2000 mg/kg bw Mallard duck Acute dietary LD50 > 5000 mg/kg diet Bobwhite quail Acute dietary LD50 > 5000 mg/kg diet Bobwhite quail Reproductive study NOAEL 1000 mg/kg diet Mallard duck Reproductive study NOAEL 1000 mg/kg diet Sheepshead minnow Acute (most sensitive) LC50 > 98 mg/L Fathead minnow Sub-chronic NOEC > 9.1 mg/L Daphnid, Daphnia magna Acute EC50 > 100 mg/L Daphnid, Daphnia magna Chronic NOEC > 2.5 mg/L Mysid, Americamysis bahia Acute EC50 > 8.0 mg/L Eastern Oyster, Shell deposition EC50 > 6.0 mg/L Crassostrea virginica Sediment dweller, Acute EC50 > 7.7 mg/kg dry sediment Chironomus riparius Duckweed, Lemna gibba Acute NOEC = 0.077 mg/L Alga, Pseudokirchneriella Acute (most sensitive) EC50 = 0.041 mg/L subcapitata Earthworm, Eisenia fetida Acute (14d) EC50 > 1000 mg/kg soil Honeybee Acute contact LD50 = 100 µg/bee

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ENVIRONMENTAL FATE Laboratory and field studies have been conducted to determine the fate of Kixor in both terrestrial and aquatic environments. Under typical conditions, Kixor was found to degrade rapidly in the environment. Environmental Fate Sorption Soil Dissipation Hydrolysis Photostability

Koc 9-56 (6 soils) Lab aerobic metabolism, DT50 15 days (4 soils) Field DT50 17 days (7 sites) Stable at pH < 7 Half-life 5 days at pH 9 DT50 29 days under soil photolysis

PHYSICAL AND CHEMICAL PROPERTIES Common Name

Saflufenacil

CAS Number

372137-35-4

Chemical Name IUPAC

N´-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydro-1(2H)pyrimidinyl) benzoyl]-N-isopropyl-N-methylsulfamide

Empirical Formula

C17H17ClF4N4O5S

Molecular Weight

500.9

Appearance

White powder

Odor

Odorless

Vapor Pressure

2.0x10-14 (Pa @ 25C)

Solubility Water Acetone Acetonitrile Methanol

pH 5: 25 mg/L pH 7: 2100 mg/L 27.5 g/100 mL 19.4 g/100 mL 2.98 g/100 mL

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BASF Agricultural Products 26 Davis Drive Research Triangle Park, NC 27709 USA +1 919-547-2000 Kixor, Integrity, OpTill, Sharpen and Treevix are trademarks of BASF. ©2009 BASF Corporation. All Rights Reserved. APN-09-01-079-0020


Kixor™ Herbicide Technical Brochure

10/12/09 2:39 PM

Kixor Herbicide Technical Brochure - Greg Cunningham

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