US 20120088667A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0088667 A1 Williams et al. (43) Pub. Date: Apr. 12, 2012

(54) SAFENINGAGENT (30) Foreign Application Priority Data (75) Inventors: Richard Williams, Colchester Apr. 7, 2009 (EP) ...... O9447OO9.3 (GB); Peter Roose, Ghent (BE): Publication Classification Johan Josef De Saegher, Ghent (51) Int. Cl. (BE) AOIN 25/32 (2006.01) AOIP 2L/00 (2006.01) (73) Assignee: TAMINCO, NAAMLOZE AOIPI3/02 (2006.01) VENNOOTSCHAP, Ghent (BE) AOIP3/00 (2006.01) AOIP 7/04 (2006.01) (21) Appl. No.: 13/263,674 (52) U.S. Cl...... 504/105:504/112:504/104:504/108; 504/110 (22) PCT Fled: Apr. 7, 2010 (57) ABSTRACT A compound selected from a composition comprising an (86) PCT NO.: PCT/B10/O1034 auxin, an auxin precursor, an auxin metabolite or a derivative of said auxin, auxin precursor or auxin metabolite and S371 (c)(1), acetaminophen or a derivative thereof for use as a plant (2), (4) Date: Dec. 27, 2011 safener.

NH, NH NH

Br

O- O OH NH H N boc Br c. CF

OMe

S. OMe Patent Application Publication Apr. 12, 2012 Sheet 1 of 16 US 2012/0088667 A1 FIG. 1(a)

ON OH On-NHH O OH

Nul OH ". Br

O OH O NH H N boc CF

OMe

OMe Patent Application Publication Apr. 12, 2012 Sheet 2 of 16 US 2012/0088667 A1

O OH O OH H 1c. N CN C O r

O OH O OH H S1 N DO Nin 1S ON

O OH O OH Patent Application Publication Apr. 12, 2012 Sheet 3 of 16 US 2012/0088667 A1

O. NH O OH NH, H NH

C

O O

N-N- O H \- NH O O HN-N- ( ) OM C N-N NH, NH NO, Patent Application Publication Apr. 12, 2012 Sheet 4 of 16 US 2012/0088667 A1

FIG. 1 (d)

C C C

C C C Patent Application Publication Apr. 12, 2012 Sheet 5 of 16 US 2012/0088667 A1

FIG. 1 (e)

OH O Os-OS-1 O. OH ON OH

HC ". ". o O. OH O. OH ON OH NH, ON OH

NH, C NH CH t 2 3

OS, OH NH, O OH O OH O NH, NH, NH OH

C F Br

O OH NH, os-NH2 O OH H NH Ns H.N NH

HN Patent Application Publication Apr. 12, 2012 Sheet 6 of 16 US 2012/0088667 A1

O. OH f ON O H N r HO

MeO OMe

O wo-)------oMeO OMe Patent Application Publication Apr. 12, 2012 Sheet 7 of 16 US 2012/0088667 A1

FG. 2

CHCOOH CHCH2CH2COOH

Os ".. Os

CH.br

(OSN H

e.g. for IAA-aspartate R: -NHCHCOOH

CHCOOH w

O Ho CHCOOH O

HSYNohCH2OH N H Patent Application Publication Apr. 12, 2012 Sheet 8 of 16 US 2012/0088667 A1 FIG. 3(a)

ACETAMINOPHENDERIVATIVES

HC O C Patent Application Publication Apr. 12, 2012 Sheet 9 of 16 US 2012/0088667 A1

FIG. 3(b)

HN CH, CH Patent Application Publication Apr. 12, 2012 Sheet 10 of 16 US 2012/0088667 A1 FIG. 3(c)

O O cif als.CH

SH

N-1- -- - -

O s CH Patent Application Publication Apr. 12, 2012 Sheet 11 of 16 US 2012/0088667 A1 FIG. 3(d)

O OH l HC NH N* O Patent Application Publication Apr. 12, 2012 Sheet 12 of 16 US 2012/0088667 A1 FIG. 3(e)

Hics CH s

rolOH Patent Application Publication Apr. 12, 2012 Sheet 13 of 16 US 2012/0088667 A1

FIG. 3(f)

OH H N

H,C

o HC

CH CH,

e H,C N Patent Application Publication Apr. 12, 2012 Sheet 14 of 16 US 2012/0088667 A1

FIG. 3(g)

H

He Sir C H O - "" O O Patent Application Publication Apr. 12, 2012 Sheet 15 of 16 US 2012/0088667 A1

FIG. 4

d s sC frch. - O N -- (OC--Oit- -sh-H-CH-O-Po, coo cH-0-Pd - - e-or Hot-choi-chro-Po, Glyceraldehyde-3-phosphate. Oy

Serine

m N. r coo N d N. -- -swamp N N H n

es co

Indole glucosinolates \ co ors. CS N". OS OS co

N -- r OSh - OS Patent Application Publication Apr. 12, 2012 Sheet 16 of 16 US 2012/0088667 A1

F.G. 5

O-CH2-COOH o-CH2 -COOH o-CH-COOH C C CH3 f

C C C C

CH2 -COOH COOH COOH C C C OCH3 US 2012/0088.667 A1 Apr. 12, 2012

SAFENINGAGENT orange, pharmaceuticals (loop diuretics such as furosemide) and UV-absorbers, as well as corrosion inhibitors for metals FIELD OF THE INVENTION and mold inhibitors in Soya sauce. Its usefulness as part of a Safening package is Surprising. 0001. This invention relates to a method and composition for improving crop safety by treating plants with, particularly 0008 Acetaminophen is widely used as an over-the but not exclusively, a composition comprising an auxin, an counter analgesic and antipyretic. It will be appreciated that auxin precursor, an auxin metabolite or a derivative of said its efficacy as part of a safening package is Surprising. auxin, auxin precursor or auxin metabolite and acetami nophen or a derivative thereof. STATEMENTS OF THE INVENTION 0009. The present invention is directed to the treatment of BACKGROUND OF THE INVENTION a plant with an effective amount of a composition comprising 0002 Chemical fertilisers, fungicides, and an auxin, an auxin precursor, an auxin metabolite or a deriva herbicides are applied to plants in order to promote growth tive of said auxin, auxin precursor or auxin metabolite and and reduce or destroy unwanted fungi, pests, weeds and other acetaminophen or a derivative thereof to improve safety. unwanted species. This is of particular importance in the field 0010. According to one aspect of the present invention of commercial farming, where obtaining the maximum yield there is provided a composition comprising an auxin, an is of the utmost importance. auxin precursor, an auxin metabolite or a derivative of said 0003 Chemical fertilisers, fungicides, pesticides, insecti auxin, auxin precursor or auxin metabolite and acetami cides and herbicides available to-date often have negative nophen or a derivative thereof for use as a plant safener. effects on crops, as well as the positive effect of reducing 0011. The combination envisaged in the present invention unwanted species and promoting growth. For example, Such may give rise to a synergistic effect. chemicals may damage the crops to which they are applied, as 0012 For ease of reference we will refer to an auxin, an well as the species to which they are targeted. This is a auxin precursor, an auxin metabolite or a derivative of said particular problem in the field of non-selective fertilisers. auxin, auxin precursor or auxin metabolite or a mixture These fertilisers, fungicides, pesticides, insecticides and her thereof as an “auxin-related compound'. bicides may also be hazardous. Other compositions applied to 0013. In one embodiment the auxin-related compound is plants such as plant growth regulators, chemical thinners and based on an indolic ring. In another embodiment the auxin abscission delay agents also often have negative effects on related compound is based on a phenolic ring. crops and may also be hazardous. 0014. In one embodiment the derivative is an acid, a con 0004 Thus, there is a continuing need for safeners and jugate, a salt, an ester, or an amide of the auxin, auxin pre which may provide improved properties. cursor, or auxin metabolite. 0015. In one embodiment the derivative is in the form of a SUMMARY OF THE INVENTION conjugate, e.g. conjugated to a Sugar, an alcohol, an amino 0005. The present invention relates to the novel use of acid, a peptide or a protein. compositions comprising an auxin, an auxin precursor, an 0016. In one embodiment the auxin precursor is choris auxin metabolite or a derivative of said auxin, auxin precursor mate, anthranilic acid, phosphoribosyl anthraniliate, 1-(O- or auxin metabolite and acetaminophenora derivative thereof carboxyphenulamino)-1-deoxyribulose-5-phosphate, for use as a plant safener. indole-3-glycerol-phosphate, indole, indole-3-acetic acid, 0006. The present invention also relates to the novel use of tryptophan, tryptamine, N-hydroxy tryptamine, indole-3-ac compounds selected from a) glucose, hydrolysed starch, etaldoxime, 1-aci-nitro-2-indolylethane, indolic glucosinate, Sucrose, fructose, glycerol, glyceraldehydes, erythrose, ribu indole-3-acetonitrile (IAN), indole-3-acetaldehyde, indole lose, Xylulose or arabinose, monosaccharides including 3-lactic acid, indole-3-pyruvic acid, or indole-3-ethanol. aldoses such as D-Ribose, D-Xylose, L-Arabinose, D-Glu 0017. In a particularly preferred embodiment the auxin cose, D-Mannose and D-Galactose; ketoses such as D-Ribu precursor is anthranilic acid or a derivative thereof. lose and D-Fructose; deoxyaldoses such as 2-Deoxy-D-ri 0018. In one embodiment the derivative of anthranilic acid bose, L-Fuccose:acetylated amino Sugars such as N-Acteyl is one of the compounds set out in FIG. 1. D-glucosamine and N-Acetyl-D-galactosamine; acidic 0019. The auxin-related compound may be a natural, such monosaccharides such as D-Glucuronic acid, L-Iduronic acid as is obtainable from seaweed or algae, or synthetic auxin. and N-Acetylneuraminic acid, Sugar alcohols such as D-Sor 0020. In one embodiment the natural auxin is indole-3- bitol and D-Mannitol, disaccharides including maltose, lac acetic acid (IAA), 4-chloro-indole-3-acetic acid (4-Cl-IAA), tose and Sucrose, or an ester or glycoside or metabolic equiva phenylacetic acid (PAA), indole-3-butyric acid (IBA), lent of such a carbohydrate; b) an organic acid of the Krebs indole-3-acetyl-1-O-B-D-glucose (IAAglc). tricarboxylic acid cycle or a metabolic precursor thereof; c) a 0021. In one embodiment the conjugate of the natural Vitamin or coenzyme, or a precursor thereof; d) a purine or auxin is IAA-Inositol, IAA-Inositol-arabinose, IAP1, an pyrimidine nucleoside, nucleotide or metabolic precursor IAA-peptide, an IAA glycoprotein, an IAA-glucan, IAA thereof; e) a naturally occurring fat or oil; or f) an amino acid aspartate, IAA-glucose, IAA-1-O-glucose, IAA-myo-Inosi in combination with the afore-mentioned compositions. Such tol, IAA-4-O-glucose, IAA-6-O-glucose, IAA-Inositol-ga compounds have previously been associated with providing lactose, an IAA amide conjugate, or an IAA-amino acid useful additive effects, but their use as part of a safening conjugate. package is Surprising. 0022. In one embodiment the synthetic auxin is 1-naph 0007 Anthranilic acid is used as an intermediate for pro thaleneacetic acid (NAA), 2,4-dichlorophenoxyacetic acid duction of dyes, pigments and saccharin. It and its esters are (2,4-D), 2-methoxy-3,6-dichlorobenzoic acid (dicamba), also used in preparing perfumes to imitate jasmine and 4-amino-3,5,6-trichloropicolinic acid (tordon), 2,4,5-trichlo US 2012/0088.667 A1 Apr. 12, 2012

rophenoxyacetic acid (2,4,5-T), 2.3.6-trichlorobenzoic acid, 0035 Moreover, according to the present invention, 4-chloro-2 methylphenoxyacetic acid (MCPA) or N,N-dim according to another aspect there is provided a safenening ethylethylthiocarbamate. composition according to the present invention further com 0023. In one embodiment the auxin metabolite is indole prising at least one of compounds (a) to (f), as described 3-lactic acid or indole-3-ethanol. above. 0024. The composition of the present invention employs 0036. The combination may give rise to a synergistic the use of acetaminophen or an analog or derivative thereof. effect. In a preferred embodiment use is made of acetaminophen. In 0037. In one embodiment therefore safener may com another embodiment the acetaminophen derivative is a com prises, e.g., at least one compound selected from c) a vitamin pound as set out in FIG. 3. or coenzyme, or a precursor thereof; d) a purine or pyrimidine 0025. In one embodiment the composition further com nucleoside, nucleotide or metabolic precursor thereof, orf) an prises cobalt. amino acid. 0026. In another aspect of the present invention there is 0038. There is further described a composition comprising provided a method for improving plant safety comprising the an effective amount of an auxin, an auxin precursor, an auxin application of a composition of the invention as described metabolite or a derivative of said auxin, auxin precursor or above to a plant or its environs or plant propagation material. auxin metabolite for use as a safener. 0027 Thus, the present invention includes a method of 0039. The treatment of a plant with an effective amount of protecting desired plants from the effect of an agrochemical the compoundanthranilic acid (also referred to as “AN”) or an comprising applying an effective amount of a composition of effective salt, ester, or amide thereof including analogs of the the present invention to the desired plant such that a protective AN and effective salts, ester and amides thereof is further effective against the agrochemical occurs. described. 0028. The composition of the present invention seeks to protect plants from damage that may occur through the appli ADVANTAGES cation of an agrochemical, preferably wihtout interfering or 0040 We have found that a composition comprising an reducing the intended effect of the agrochemical. For auxin, an auxin precursor, an auxin metabolite or a derivative example, a safener in the context of the application of a of said auxin, auxin precursor or auxin metabolite and herbicide protects crop plants from herbicide damage without acetaminophen or a derivative thereofis (amongst other ben reducing activity in target weed species. efits in plants) an effective safening agent, wherever this is 0029. The composition of the present invention can be deemed useful. applied as a mixture with the agrochemical or before or after 0041. We have found that a compound selected from a) it glucose, hydrolysed Starch, Sucrose, fructose, glycerol, glyc 0030 Thus, we provide a kit for use in crops comprising eraldehydes, erythrose, ribulose, Xylulose or arabinose or an the agrochemical, and the components of the present inven ester or glycoside, monosaccharides including aldoses Such tion, preferably in separate containers. as D-Ribose, D-Xylose, L-Arabinose, D-Glucose, D-Man 0031. The agrochemical may be, for example, at least one nose and D-Galactose; ketoses such as D-Ribulose and of a fungicide, an , a herbicide, a fertiliser, a plant D-Fructose; deoxyaldoses such as 2-Deoxy-D-ribose, L-Fuc growth regulator, a chemical thinning agent and an abscission cose; acetylated amino Sugars such as N-Acteyl-D-glu delay agent. cosamine and N-Acetyl-D-galactosamine; acidic monosac 0032. Thus, in one embodiment the composition further charides such as D-Glucuronic acid, L-Iduronic acid and comprises at least one of a fungicide, an insecticide, a herbi N-Acetylneuraminic acid, Sugar alcohols such as D-Sorbitol cide, a fertiliser, a plant growth regulator, a chemical thinning and D-Mannitol, disaccharides including maltose, lactose agent and an abscission delay agent. and Sucrose, or metabolic equivalent of such a carbohydrate; 0033. It will be appreciated that the components of the b) an organic acid of the Krebs tricarboxylic acid cycle or a safening composition and the compound it is safening against metabolic precursor thereof; c) a vitamin or coenzyme, or a should be different. precursor thereof; d) a purine or pyrimidine nucleoside, 0034. There is also described a compound selected from a) nucleotide or metabolic precursor thereof; e) a naturally glucose, hydrolysed Starch, Sucrose, fructose, glycerol, glyc occurring fat or oil; or f) an amino acid is (amongst other eraldehydes, erythrose, ribulose, Xylulose or arabinose, benefits in plants) an effective Safening agent, wherever this is monosaccharides including aldoses Such as D-Ribose, D-Xy deemed useful. lose, L-Arabinose, D-Glucose, D-Mannose and D-Galactose; 0042. We have also found that a composition comprising ketoses such as D-Ribulose and D-Fructose; deoxyaldoses an auxin, an auxin precursor, an auxin metabolite or a deriva Such as 2-Deoxy-D-ribose, L-Fuccose:acetylated amino Sug tive of said auxin, auxin precursor or auxin metabolite or a ars such as N-Acteyl-D-glucosamine and N-Acetyl-D-galac mixture thereofis (amongst other benefits in plants) an effec tosamine; acidic monosaccharides such as D-Glucuronic tive Safening agent, wherever this is deemed useful. acid, L-Iduronic acid and N-Acetylneuraminic acid, Sugar 0043. We have found that the present invention can pro alcohols such as D-Sorbitol and D-Mannitol, disaccharides vide a reduction in phytotoxicity in crops treated with fungi including maltose, lactose and Sucrose, or an ester or glyco cides, fertilizers, herbicides and pesticides, as well as plant side or metabolic equivalent of Such a carbohydrate; b) an growth regulators, chemical thinning agents and abscission organic acid of the Krebs tricarboxylic acid cycle or a meta delay agents. bolic precursor thereof; c) a vitamin or coenzyme, or a pre 0044) We have also found that the safening systems of the cursor thereof; d) a purine or pyrimidine nucleoside, nucle present invention can be used alone (without e.g. fungicides, otide or metabolic precursor thereof; e) a naturally occurring fertilizers, herbicides, pesticides) to provide a boost in growth fat or oil; or f) an amino acid for use as a safener. and/or vigour, especially when applied under conditions of US 2012/0088.667 A1 Apr. 12, 2012

potential or actual plant stress, such as high/low pH, high/low Went's results indicated that the curvatures of stems were temperatures, high/low salinity, drought or other unfavour proportional to the amount of growth Substance in the agar. able plant conditions. This test is also called the avena curvature test. Other func 0045. The composition of the present invention may tional tests which can be employed to determine auxin activ include trace elements such as iron, manganese, boron, cop ity include the ability to cause rooting in stem cuttings and the per, cobalt, molybdenum and zinc. In a particularly preferred ability to promote cell division in tissue or cell culture. embodiment, the composition of the present invention 0059 A review of auxins, their synthesis and metabolism includes cobalt. We have found that cobalt increases nodula can be found in e.g. Normanly, Slovin and Cohen in “Plant tion in nitrogen fixing crops. Hormones, Biosynthesis, Signal Transduction and Action. 0046. The combinations envisaged in the compositions of Ed Peter J. Davies, 2004 Chapter “B1. Auxin Biosynthesis the present invention may give rise to a synergistic effect. and Metabolism' pages 36-62. 0060. In addition to indolic auxins, various phenolic aux BRIEF DESCRIPTION OF THE FIGURES ins have auxin activity. 0047 FIG. 1 shows structures of examples of analogs of 0061 Some examples of naturally occurring auxins and anthranilic acid. Some examples of the lower molecular weight conjugates 0048 FIG. 2 shows structures of examples of naturally which may be used in the present invention are shown in FIG. occurring auxins and conjugates. 2. 0049 FIG. 3 shows structures of examples of derivatives 0062. The present invention may also make use of conju of acetaminophen. gates. It is believed that plants use conjugates for storage 0050 FIG. 4 shows an overview of the reactions leading purposes and/or to regulate the amount of free auxin available from chorismate to IAA and tryptophan. in the plant. IAA is primarily conjugated to the amino acid 0051 FIG.5 shows the structure of some synthetic auxins. aspartate. 0063 Related low molecular weight conjugates, such as DETAILED DESCRIPTION OF THE INVENTION IAA-Inos, IAA-Inos-arabinose and conjugates with other amino acids, and higher molecular weight conjugates, such as 0052 Various preferred features and embodiments of the the IAA protein IAP1, IAA-peptides, IAA glycoprotein and present invention will now be described by way of non IAA-glucans, have also been isolated from plants. limiting example. 0064 IAA and its precursors undergo metabolic conver 0053. The present invention relates to the use of anthra sions to indole-3-lactic acid, indole-3-ethanol and IBA. IBA nilic acid (AN): has been found to occur naturally in plants; although some references refer to it as a synthetic auxin. Some commentators refer to it as an auxin perse and other as a precursor to IAA. 0065 One general class of conjugated forms consists of those linked through carbon-oxygen-carbon bridges. These OH compounds have been referred to generically as “ester linked’, although some 1-0 Sugar conjugates Such as 1-O- IAA-Gluc are actually linked by acyl alkyl acetal bonds. Typical ester-linked moieties include 6-O-IAGluc, IAA-Inos, IAA-glycoproteins, IAA-glucans and simple methyl and 0054 AN, also known as anthraniliate, has the CAS num ethyl esters. The other type of conjugates present in plants are ber 118-92-3. linked through carbon-nitrogen-carbon amide bonds (re 0055 We have described useful derivatives of AN above. ferred to as "amide-linked'), as in the IAA-amino acid and Preferably such derivatives are water soluble. Representative protein and peptide conjugates (see FIG. 2). salts include inorganic salts such as ammonium, lithium, 006.6 Biochemical pathways that result in IAA production Sodium, potassium, magnesium and calcium salts and organic within a plant tissue include: (A) de novo synthesis, whether amine salts such as the triethanolamine, dimethylethanola from tryptophan referred to as Trp-dependent (Trp-D) IAA mine and ethanolamine salts. synthesis, or from indolic precursors of Trp referred to as 0056. The present invention involves the use of auxins. Trp-independent (Trp-I) IAA Synthesis, since these pathways 0057 Auxins are a class of plant growth hormones. An bypass Trp; (B) hydrolysis of both amide- and ester-linked auxin is an organic Substance that promotes cell elongation IAA conjugates; (C) transport from one site in the plant to growth when applied in low concentrations to plant tissue another site; and (D) conversion of IBA to IAA. IAA turnover segments in a bioassay. The most studied member of the auxin mechanisms include: (E) oxidative catabolism; (F) conjugate family is indole-3-acetic acid (IAA). In addition to IAA, there synthesis; (G) transport away from a given site; and (H) are several other naturally occurring auxins that have been conversion of IAA to IBA. The present invention makes use described to date: IAA, IBA, PAA and 4-Cl-IAA. Naturally of Such precursors and metabolites along this pathway. The occurring auxins are found in plants as the free acid and in present invention does not make use of inactive metabolites, conjugated forms. Such as arise from catabolism of the auxin. 0058 An auxin has been defined as a compound that gives 0067. Normally the present invention makes use of the rise to curvature in the grass coleoptile curvature (or growth) tryptophan-dependent pathway. A Summary of the reactions test. Such an assay is described by Fritz Went in 1926 and leading from chorismate—the first committed step of indolic 1928. In this bioassay coleoptile tips of grass seedlings are metabolism—to IAA and tryptophan is shown in FIG. 4. placed on an agar plate containing the Substance to be 0068. The present invention also encompasses the use of assayed. If an auxin response is present then the coleoptile synthetic auxins. Some examples of synthetic auxins are bends in darkness and the angle of curvature can be measured. shown in FIG. 5. US 2012/0088.667 A1 Apr. 12, 2012

0069. A comparison of the compounds that possess auxin L-Fuccose; acetylated amino Sugars such as N-Acteyl activity reveals that at neutral pH they all have a strong nega D-glucosamine and N-Acetyl-D-galactosamine; acidic tive charge on the carboxyl group of the side chain that is monosaccharides such as D-Glucuronic acid, L-Idu separated from a weaker positive charge on the ring structure ronic acid and N-Acetylneuraminic acid, Sugar alcohols by a distance of about 0.5 nm. It has been proposed that an such as D-Sorbitol and D-Mannitol, disaccharides indole is not essential for activity, but that it can be an aro including maltose, lactose and Sucrose, or an ester or matic or fused aromatic ring of a similar size. A model has glycoside or metabolic equivalent of Such a carbohy been proposed as being a planar aromatic ring-binding plat drate, which will normally be applied at 10 to 10,000 form, a carboxylic acid-binding site and a hydrophobic tran g/ha (grams per hectare). Without wishing to be bound sition region that separates the two binding sites. by any theory the component may function as 0070 The present invention involves the use of acetami 0079 (1) A source for the production of high energy nophen. bonds as inadenosine trisephosphate (ATP) production, 0071 Acetaminophen has the IUPAC name, N-(4-hydrox 0080 (2) For the formation of reduced nicotinamide ypheyl)acetamide and is commonly referred to as paraceta adenine dinucleotide (NADH) and reduced nicotamide mol. It has the CAS number 103-90-2. adenine dinucleotide phosphate (NADPH) and 0072. Its formula is: 0081 (3) As precursors of amino acids and nucleotides: 0082 (b) an organic acid of the Krebs Tricarboxylic Acid Cycle or a metabolic precursor thereof (including H citric, succinic, malic, pyruvic, acetic and fumaric acids), which will normally be applied at similar rates to N and used for similar functions as the carbohydrate O Source; HO 0.083 (c) a vitamin or coenzyme, e.g. thiamine, ribofla vin, pyridozine, pyridoxamine, pyridoxal, nicotinamide, 0073. As described above, derivatives of acetaminophen folic acid, or a precursor thereof including nicotinic are also useful in the present invention. acid, which will normally be applied at 0.01 to 500 g/ha 0074 The compounds or compositions of the present to stimulate metabolic processes dependent on enzy invention can be used in combination with other components, matic action; as appropriate. 0084 (d) a purine or pyrimidine nucleoside, nucleotide 0075. The present invention provides the use in a safening or a metabolic precursor thereof, e.g. adenine, adenos composition of a compound selected from a) glucose, ine, thymine, thymidine, cytosine, guanine, guanosine, hydrolysed Starch, Sucrose, fructose, glycerol, glyceralde hypoxanthine, uracil, uridine or inosine, which will nor hydes, erythrose, ribulose, Xylulose or arabinose, monosac mally be applied at 1 to 500 g/ha to act as structural charides including aldoses Such as D-Ribose, D-Xylose, precursors for nucleic acid synthesis; L-Arabinose, D-Glucose, D-Mannose and D-Galactose; 0085 (e) a naturally occurring fat or oil including olive, ketoses such as D-Ribulose and D-Fructose; deoxyaldoses Soya, coconut and corn oils, which can be degraded by Such as 2-Deoxy-D-ribose, L-Fuccose:acetylated amino Sug living organisms to fatty acids and which will normally ars such as N-Acteyl-D-glucosamine and N-Acetyl-D-galac be applied at 10 to 10,000 g/ha; tosamine; acidic monosaccharides such as D-Glucuronic I0086 (f) an amino acid of a type that occurs naturally in acid, L-Iduronic acid and N-Acetylneuraminic acid, Sugar plant proteins, e.g. glycine, alanine, Valine, leucine, iso alcohols such as D-Sorbitol and D-Mannitol, disaccharides leucine, serine, threonine, cysteine, methionine, aspartic including maltose, lactose and Sucrose, or an ester or glyco acid, glutamic, acid, glutamine, asparagine, lysine, side or metabolic equivalent of Such a carbohydrate; b) an hyroxylysine, arginine, histidine, phenylalanine, organic acid of the Krebs tricarboxylic acid cycle or a meta tyrosine, tryptophan, proline or hydroxyproline, which bolic precursor thereof; c) a vitamin or coenzyme, or a pre will normally be applied at 1 to 500 g/ha to act as struc cursor thereof; d) a purine or pyrimidine nucleoside, nucle tural units for newly formed proteins or by their degra otide or metabolic precursor thereof; e) a naturally occurring dation to function in a similar manner to fatty acids and fat or oil; or f) an amino acid in Some embodiments. carbohydrates. 0076. By “effective amount' we include an amount of the I0087. Other ingredients such as adjuvants may be added to compound or composition of the present invention which is the safening Solution. The adjuvants can facilitate spreading Sufficient to achieve the desired “safening response'. In gen and efficacy, and improve the adhesion properties of the com eral by 'safening response' we mean protecting the crop position, and generally include oils, antifoaming agents and plants whilst not reducing the activity of the active ingredient Surfactants. Such components which are useful in the present being applied to the crop. invention include, but are not limited to: terpene, Brij family 0077. The compound may be defined as belonging to one (polyoxyethylene fatty alcohol ether) from Uniqema (Castle, or more of the following classes (a) to (f); although two or Del.); surfactant in Tween family (Polyoxyethylene sorbitan more such additives in the same or different classes may be esters) from Uniqema (Castle, Del.); Silwet family (Organo used: silicone) from Union Carbide (Lisle, Ill.); Triton family (Oc 0078 (a) glucose, hydrolysed starch, sucrose, fructose, tylphenol ethoxylate) from The Dow Chemical Company glycerol, glyceraldehyde, erythrose, Xylulose or arabi (Midland, Mich.); Tomadol family (ethoxylated linear alco nose, monosaccharides including aldoses such as D-Ri hol) from Tomaha Products, Inc. (Milton, Wis.); Myri family bose, D-Xylose, L-Arabinose, D-Glucose, D-Mannose (Polyoxyethylene (POE) fatty acid esters) from Uniqema and D-Galactose; ketoses such as D-Ribulose and (Castle, Del.); Span family (Sorbitan ester) from Uniqema D-Fructose; deoxyaldoses such as 2-Deoxy-D-ribose, (Castle, Del.); and Trylox family (Ethoxylated Sorbitol and US 2012/0088.667 A1 Apr. 12, 2012

Ethoxylated Sorbitol Esters) from Cognis Corporation (Cin 0093. Non-limiting examples of insecticides in relation to cinnati, Ohio) as well as commercial Surfactant Latron which the composition of the present invention may be useful B-1956 (77.0% modified phthalic/glycerol alkyl resin and include chlorinated hydrocarbons such as , , 23.0% Butyl alcohol) from Rohm & Haas (Philadelphia, Pa.); , DDT, , , , Hep Caspil (Blend of Polyether-polymethylsiloxanecopolymer tachlor, Hexachlorobenzene, (gamma-Hexachloro and nonionic Surfactant) from Aquatrols (Paulsboro, N.J.); cyclohexane), , , Pentachlorophenol, Agral 90 (Nonyl phenol ethoxylate) from Norac Concept, TDE; organophosphates Such as , AZinphos-methyl, Inc. (Orleans, Ontario, Canada); Kinetic (99.00% Proprietary , , , Chlorpyriphos blend of polyalkyleneoxide modified polydimethylsiloxane methyl, , (DDVP), , and nonionic Surfactants) from Setre Chemical Company , , Ethoprop, , Feni (Memphis, Tenn.); and Regulaid (90.6% 2-butoxyethanol, trothion, , Fosthiazate, , , poloxalene, monopropylene glycol) from KALO, Inc. (Over , , , , Oxydemeton land Park, Kans.). methyl, , Parathion-methyl, , , 0088. When the final solution is to be applied to plants , Phostebupirim, , Pirimiphos-methyl, Pro which, because of their hairy or waxy surface, may be difficult fenofos, , , Tribufos, Trichlorfon; to wet, it may be particularly advantageous to include Such such as . , , Fenoxy other additives, commonly known in the agrochemical indus carb, , 2-(1-Methylpropyl)phenyl methylcarbam try, such as Surfactants, wetting agents, spreaders and Stick ate; Phenothiazine: such as Allethrin, , ers. (Examples of wetting agents include silicone surfactants, , , Lambda-, Per nonionic Surfactants such as alkyl ethoxylates, anionic Sur methrin, , , , Trans factants such as phosphate ester salts and amphoteric or cat fluthrin, such as , , ionic Surfactants such as fatty acid amido alkyl betaines). , Nitenpyram, . . Thia methoxam; plant derived such as Caffeine, Derris (rotenone), 0089. The compounds of the invention may be the sole Anabasine, Anethole, Annonin, Asimina, Azadirachtin, active ingredient of the composition or they may be admixed Carapa, Cinnamon leaf oil, Cinnamaldehyde, Cinnamyl with further active ingredients such as nematicides, insecti acetate, Deguelin, Derris, Desmodium caudatum, Eugenol, cides, synergists, herbicides, fungicides, fertilisers, chemi Linalool, Myristicin, Neem (Azadirachtin), Nicotiana rustica cally thinning agents, abscission delay agents or plant growth (Nicotine), Peganum harmala, Oregano oil, Polyketide, Pyre regulators where appropriate. thrum, Ouassia, Tetranortriterpenoid, Thymol. 0090. In a particularly preferred embodiment, the one or 0094. Non-limiting examples of fungicides in relation to more compounds of the invention are administered in com which the composition of the present invention may be useful bination optionally with one or more active agents. In Such include (3-ethoxypropyl)mercury bromide, 2-methoxyeth cases, the compounds of the invention may be administered ylmercury chloride, 2-phenylphenol, 8-hydroxyquinoline consecutively, simultaneously or sequentially with each other Sulfate, 8-phenylmercurioxyquinoline, acilbenzolar, acy or the one or more active agents. The major advantages of lamino acid fungicides, acy petacs, aldimorph, aliphatic nitro combining the compounds are that it may promote additive or gen fungicides, allyl alcohol, amide fungicides, ampropylfos. possible synergistic effects through e.g. biochemical interac anilazine, anilide fungicides, antibiotic fungicides, aromatic tions. Beneficial combinations may be suggested by studying fungicides, aureofungin, azaconazole, azithiram, aZOX the activity of the test compounds. This procedure can also be ystrobin, barium polysulfide, benalaxyl, benalaxyl-M, beno used to determine the order of administration of the agents, danil, benomyl, benquinox, bentaluron, benthiavalicarb, ben i.e. before, simultaneously or after delivery. Zalkonium chloride, benzamacril, benzamide fungicides, 0091. In order to apply the composition to the plant or benZamorf, benzanilide fungicides, benzimidazole fungi environs of the plant, the composition may be used as a cides, benzimidazole precursor fungicides, benzimidazolyl concentrate or more usually is formulated into a composition fungicides, benzohydroxamic acid, benzothiazole which includes an effective amount of the composition of the fungicides, bethoxazin, binapacryl, biphenyl, bitertanol, present invention together with a suitable inert diluent, carrier bithionol, bixafen, blasticidin-S, Bordeaux mixture, boscalid, material and/or Surface active agent. Preferably the compo bridged diphenyl fungicides, bromuconazole, bupirimate, sition is in the form of an aqueous solution which may be Burgundy mixture, buthiobate, butylamine, calcium polysul prepared from the concentrate. By effective amount we mean fide, captafol, captan, carbamate fungicides, carbamorph, that the composition (and/or its individual components) pro carbanilate fungicides, carbendazim, carboxin, carpropamid, vides an improved effect. carvone, Cheshunt mixture, chinomethionat, chlobenthiaz 0092. The applied concentration of chemical can vary one, chloraniformethan, chloranil, chlorfenazole, chlorodini widely depending on the water Volume applied to plants as tronaphthalene, chloroneb, chloropicrin, chlorothalonil. well as other factors such as plant age and size, and plant chlorquinox, chloZolinate, ciclopirox, climbazole, clotrima sensitivity to the product. Typical rates of AN-related com Zole, conazole fungicides, conazole fungicides (imidazoles), pounds would be 1-10g/ha (preferably and as used in these conazole fungicides (triazoles), copper(II) acetate, copper(II) trials, 1 g per hectare was applied), typical rates of acetami carbonate, basic, copper fungicides, copper hydroxide, cop nophen or its derivatives would be 1-10 g/ha (preferably and per naphthenate, copper oleate, copper oxychloride, copper as used in these trials, 3 g per hectare was applied). Typical (II) sulfate, copper Sulfate, basic, copper Zinc chromate, rates of the agrochemically acceptable additive of the present cresol, cufraneb, cuprobam, cuprous oxide, cyaZofamid, invention would be 1-10g/ha (preferably and as used in these cyclafuramid, cyclic dithiocarbamate fungicides, cyclohex trials, less than 3 g per hectare was applied). The rate of other imide, cyflufenamid, cymoxanil, cypendazole, cyprocona components such as spreaders and stickers can be 50-200 ml Zole, cyprodinil, dazomet, DBCP debacarb, decafentin, per ha. dehydroacetic acid, dicarboximide fungicides dichlofluanid, US 2012/0088.667 A1 Apr. 12, 2012 dichlone, dichlorophen, dichlorophenyl, dicarboximide fun Sodium pentachlorophenoxide, sodium polysulfide, SpiroX gicides, dichloZoline, diclobutraZol, diclocymet, diclomez amine, streptomycin, strobilurin fungicides, Sulfonanilide ine, dicloran, diethofencarb, diethyl pyrocarbonate, difeno fungicides, sulfur, Sultropen, TCMTB, tebuconazole, conazole, diflumetorim, dimethirimol, dimethomorph, tecloftalam, tecnaZene, tecoram, tetraconazole, thiabenda dimoxystrobin, diniconazole, diniconazole-M, dinitrophenol Zole, thiadifluor, thiazole fungicides, thicyofen, thifluzamide, fungicides, dinobuton, dinocap, dinocap-4, dinocap-6, dinoc triforine, thiocarbamate fungicides, thiochlorfemphim, thi ton, dinopenton, dinosulfon, dinoterbon, diphenylamine, omersal, thiophanate, thiophanate-methyl, thiophene fungi dipyrithione, disulfuram, ditalimfos, dithianon, dithiocar cides, thioquinox, thiram, tiadinil, tioxymid, tiVedo, tolclo bamate fungicides, DNOC, dodemorph, dodicin, dodine, fos-methyl, tolnaftate, tolylfluanid, tolylmercury acetate, DONATODINE, drazoxolon, edifenphos, epoxiconazole, triadimefon, triadimenol, triamiphos, triarimol, triaZbutil, tri etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, eth azine fungicides, triazole fungicides, triaZoxide, tributyltin ylmercury 2,3-dihydroxypropyl mercaptide, ethylmercury oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, acetate, ethylmercury bromide, ethylmercury chloride, eth triflumizole, triforine, triticonazole, unclassified fungicides, ylmercury phosphate, etridiazole, famoxadone, fenamidone, Undecylenic acid, uniconazole, uniconazole-P. urea fungi fenaminosulf, fenapanil, fenarimol, fenbuconazole, fen cides, validamycin, valinamide fungicides, VincloZolin, furam, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fen Zarilamid, Zinc naphthenate, Zineb, Ziram, Zoxamide. propidin, fenpropimorph, fentin, ferbam, ferimZone, fluazi nam, fludioxonil, flumetover, flumorph, fluopicolide, 0.095 Non-limiting examples of fertilizers in relation to fluoroimide, fluotrimazole, fluoxastrobin, fluguinconazole, which the composition of the present invention may be useful flusilazole, flusulfamide, flutolanil, flutriafol, folpet, formal include nitrogen fertilizers such as ammonium, ammonium dehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, fura Sulphate, ammonium chloride, ammonium Sulphate nitrate, mide fungicides, furanilide fungicides, furcarbanil, furcona ammonium nitrate, calcium ammonium nitrate, sodium Zole, furconazole-cis, furfural, furmecyclox, furophanate, nitrate, calcium nitrate, potassium nitrate, urea; phosphate glyodin, griseofulvin, guaZatine, halacrinate, hexachloroben fertilizers such as single Superphosphate, triple Superphos Zene, hexachlorobutadiene, hexachlorophene, hexaconazole, phate, diammonium phosphate, monoammonium phosphate, hexylthiofos, hydrargaphen, hymexaZol, imazalil, imiben ground phosphate rock, rock phosphate, rock phosphate; pot conazole, imidazole fungicides, iminoctadine, inorganic fun ash fertilizers such as muriate of potash (potassium chloride), gicides, inorganic mercury fungicides, iodomethane, ipcona Sulphate of potash, Sulphate of potash magnesia; magnesium Zole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, fertilizers such as kieserite, epsom salts, magnesium sulfate isovaledione, kasugamycin, kresoxim-methyl, Lime Sulfur (Epsom salts); complex fertilizers such as urea-ammonium (lime Sulphur), mancopper, mancoZeb, maneb, mebenil. nitrate NPK fertilizers, NP fertilizers, NK fertilizers and PK mecarbinzid, mepanipyrim, mepronil, mercuric chloride, fertilizers; aluminium sulfate, Ferrous sulfate, phosphite fer mercuric oxide, mercurous chloride, mercury fungicides, tilizers; thiosulphate fertilizers. metalaxyl, metalaxyl-M (a.k.a. Mefenoxam), metam, meta 0096. Non-limiting examples of plant growth regulators in ZOXolon, metconazole, methasulfocarb, methfuroxam, relation to which the composition of the present invention methyl bromide, methyl isothiocyanate, methylmercury ben may be useful include abscisic acid or a derivative thereof, a Zoate, methylmercury dicyandiamide, methylmercury pen cytokinin, ethylene or a gibberlin. tachlorophenoxide, metiram, metominostrobin, 0097. Non-limiting examples of the plant growth regula metrafenone, metSulfoVax, milineb, morpholine fungicides, tor in relation to which the composition of the present inven myclobutanil, mycloZolin, N-(ethylmercury)-p-toluene tion may be useful include p-Chlorophenoxyacetic acid Sulfonanilide, nabam, natamycin, nystatin, nitrostyrene, (4-CPA), 2-CPA, 2,4-Dichlorophenoxyacetic acid, 2,4- nitrothal-isopropyl, nuarimol, OCH, octhillinone, ofurace, Dichlorophenoxyacetic acid Sodium salt, Indole-3-acetic oprodione, organomercury fungicides, organophosphorus acid Free acid (IAA), Indole-3-acetic acid Sodium salt, fungicides, organotin fungicides, orysastrobin, oxadixyl, Indole-3-acetic acid methyl ester, Indole-3-acety-L-aspartic Oxathiin fungicides, oxazole fungicides, oxine copper, Oxpo acid, Indole-3-butyric acid (IBA), Indole-3-butyric acid conazole, oxycarboxin, pefurazoate, penconazole, pencycu Potassium salt (K-IBA), alpha-Naphthaleneacetic acid Free ron, pentachlorophenol, penthiopyrad, phenylmercuriurea, acid (NAA), beta-Naphthoxyacetic acid Free acid (NOA), phenylmercury acetate, phenylmercury chloride, phenylmer Phenylacetic acid (PAA), Picloram, 2,4,5-Trichlorophenoxy cury derivative of pyrocatechol, phenylmercury nitrate, phe acetic acid (2,4,5-T), 2,3,5-Triiodobenzoic acid Free acid nylmercury Salicylate, phenylsulfamide fungicides, phos (TIBA), Adenine Free base, Adenine hemisulfate salt, 6-Ben diphen, phthalide, phthalimide fungicides, picoxystrobin, Zylaminopurine (BA), 6-Benzylaminopurine Hydrochloride, piperalin, polycarbamate, polymeric dithiocarbamate fungi N-Benzyl-9-(2-tetrahydropyranyl) adenine (BPA), N-(2- cides, polyoxins, polyoxorim, polysulfide fungicides, potas Chloro-4-pyridyl)N'-phenylurea (4-CPPU), 6-(gamma, sium azide, potassium polysulfide, potassium thiocyanate, gamma-Dimethylallylamino)purine (2iP), 1,3-Diphenylurea probenazole, prochloraz, procymidone, propamocarb, propi (DPU), Kinetin, Kinetin Hydrochloride, 1-Phenyl-3-(1,2,3- conazole, propineb, produinazid, prothiocarb, prothiocona thiadiazol-5-yl)urea, trans-Zeatin Free base, Zeatin, trans Zole, pyracarbolid, pyraclostrobin, pyrazole fungicides, pyra Zeatin Hydrochloride, trans-Zeatin riboside, (+)-cis, trans Zophos, pyridine fungicides, pyridinitril, pyrifenox, Abscisic acid (ABA), Ancymidol, Chlorocholine chloride pyrimethanil, pyrimidine fungicides, pyroquilon, pyroxy (CCC), chlormeduat chloride--choline chloride (5C chlo chlor, pyroxyfur, pyrrole fungicides, quinacetol, quinaZamid, rmeduat), 3,6-Dichloro-o-anisic acid (Dicamba), Gibberellic quinconazole, quinoline fungicides, quinomethionate, acid (GA), Gibberellic acid Potassium salt (K-GA), Gib quinone fungicides, quinoxaline fungicides, quinoxyfen, berellin A Free acid (GA), (t)-jasmonic acid, Phlorogluci quintoZene, rabenzazole, Salicylanilide, silthiofam, sim nol, N-(Phosphonomethyl)glycine (Glyphosate). Succinic econazole, sodium azide, Sodium orthophenylphenoxide, acid 2.2-dimethylhydrazide, trinexapacethyl or metconazole. US 2012/0088.667 A1 Apr. 12, 2012

0098. The plant growth regulator may be other than a picolinafen, oxadiargyl; carboxylic acids such as picloram, naturally occurring plant hormone. triclopyr, fluoroxypyr, clopyralid, quinclorac, pyridines Such 0099 Further non-limiting examples of the plant growth as dithiopyr, thiazopyr, Sulfonylureas Such as chlorSulfuron, regulator include antiauxins, such as: clofibric acid and 2.3, chlorimuron-ethyl, metSulfuron-methyl, Sulfometuron-me 5-tri-iodobenzoic acid; auxins such as 4-CPA, 2,4-D, 2,4-DB, thyl, halosulfuron-methyl, sulfometuron-methyl, bensulfu 2,4-DEP, dichlorprop, fenoprop, IAA, IBA, naphthaleneac ron, nicosulfuron, triasulfuron, primisulfuron-methyl, ami etamide, C.-naphthaleneacetic acid, 1-naphthol, naphthoxy dosulfuron, azimsulfuron, cyclosulfamuron, acetic acid, potassium naphthenate, sodium naphthenate, 2.4. ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron 5-T; cytokinins such as 2iP. benzyladenine, kinetin, Zeatin: methyl, foramsulfuron, iodosulfuron-methyl, mesosulfuron defoliants such as calcium cyanamide, dimethipin, endothal, methyl, oxasulfuron, prosulfuron, rimsulfuron, Sulfo Sulfu ethephon, merphos, metoxuron, pentachlorophenol, thidi ron, tribenuron-methyl, trifloxysulfuron, triflusulfuron aZuron, tribufos; ethylene inhibitors such as aviglycine, methyl, tritosulfuron, foramsulfuron, iodosulfuron-methyl, 1-methylcyclopropene; ethylene releasers such as ACC, eta thiocarbamates such as EPTC, pebulate, thiobencarb, buty celasil, ethephon, glyoxime; gibberellins such as gibberel late, cycloate, molinate, Vernolate, diallate, triallate; triazines lins, gibberellic acid; growth inhibitors such as abscisic acid, Such as atrazine, prometryn, ametryn, and terbutryne; triazi ancymidol, butralin, carbaryl, chlorphonium, chlorpropham, nones such as metribuzin and hexaZinone; triazoles such as dikegulac, flumetralin, fluoridamid, fosamine, glyphosine, amitrol; uracils such as bromacil, terbacil, lenacil; benzoyl isopyrimol, jasmonic acid, maleic hydrazide, mepiduat, cyclohexanediones such as mesotrione, Sulcotrione, ben mepiduat chloride, piproctanyl, prohydrojasmon, propham, Zofenap, N-phenyl-phthalimides-cinidon-ethyl, oxazo 2,3,5-tri-iodobenzoic acid; morphactins such as chlorfluren, lidinediones Such as pentoxazone; phenyl-pyrazoles such as chlorflurenol, dichlorflurenol, flurenol; growth retardants pyraflufen-ethyl; pyrimidindiones such as butafenacil; Sul Such as chlormeduat, daminozide, flurprimidol, mefluidide, fonyamino-carbonyl-triazolinones such as flucarbaZone, pro paclobutraZol tetcyclacis, uniconazole; growth stimulators poxycarbazone; tetrazolinones Such as fentraZamide; triaz Such as brassinolide, forchlorfenuron, hymexaZol; and olinones Such as amicarbazone; flufenpyr-ethyl; unclassified plant growth regulators such as benzofluor, OXOZiclomefone; benzobicyclon; soaps; petroleum oils. buminafos, carvone, ciobutide, clofencet, cloxyfonac, cyana 0101. Non-limiting examples of abscission delay agents in mide, cyclanilide, cycloheximide, cyprosulfamide, epoc relation to which the composition of the present invention holeone, ethychloZate, ethylene, fenridazon, heptopargil, may be useful include 1-naphthaleneacetic acid (NAA), holoSulf, inabenfide, karetazan, lead arsenate, methasulfo NAAm, 2,4-D, 2,4,5-T 2.4.5-TP, amino-oxyacetic acid, ami carb, prohexadione, pydanon, Sintofen, triapenthenol, trinex noethoxyvinylglycine (AVG) and daminozide. apaC. 0102. It will be appreciated that the active ingredient and 0100. Non-limiting examples of herbicides in relation to safener should be different to each other. which the composition of the present invention may be useful 0103) The composition of the present invention may also include aminopyralid, glufosinate ammonium, fluoroxypyr, include trace elements such as iron, manganese, boron, cop imazapic, pendimethlin, Sodium chlorate, chloroacetamindes per, cobalt, molybdenum and zinc. Preferably, the trace ele Such as metalchlor, acetochlor, butachlor, propachlor, thenyl ment is cobalt. In one embodiment cobalt is in the form of chlor; amides such as dimethenamid, propanil, naptalam, cobalt sulphate. pronamide, bensulide, pethoxamid; organoarsenicals such as 0104. In a particularly preferred embodiment, the one or cacodylic acid and its sodium salt, disodium methanearson more compounds of the invention are administered in com ate, monosodium methanearsonate; benzoic acids and deriva bination optionally with one or more active agents. In Such tives thereof Such as dicamba, chlorfenac, chloramben; cases, the compounds of the invention may be administered nitriles such as dichlobenil and bromoxynil, 2,6-dichloroben consecutively, simultaneously or sequentially with each other Zonitrile, Ioxynil; benzothiadiazoles such as bentaZone; bipy or the one or more active agents. The major advantages of ridyliums such as diguat, paraquat, difenZoquat; carbamates combining the compounds are that it may promote additive or Such as propham, chloropropham, asulam, phenyl-carbam possible synergistic effects through e.g. biochemical interac ates Such as phenmedipham, desmedipham; chlorinated ali tions. Beneficial combinations may be suggested by studying phatic acids such as TCA, dalapon; cyclohexanediones Such the activity of the test compounds. This procedure can also be as Sethoxydim, clethodim, cycloxydim, tralkoxydim, tepral used to determine the order of administration of the agents, oxydim; dinitroanilines such as benefin, oryzalin, pen i.e. before, simultaneously or after delivery. dimethalin, isopropalin; dinitrophenols such as DNOC, 0105. The rate and timing of application will depend on a DINOSEB; diphenyl ethers such as nitrophen, bifenox, fome number of factors knownto those skilled in theart, such as the safen, acifluorfen, lactofen, oxyfluorfen: imidazolinones type of species etc. A second or further application(s) can be Such as imaZamox, imazapyr, imazaquin, imazamethabenz made as appropriate. The timings between each application methyl, imazethapyr; triazolopyrimidines Such as flumetsu may be in the region of 5 days or more. lam, metoSulam, chloranSulam, disclosulam: aryloxphenoxy 0106 The present invention relates to a method of safen propionates Such as fluaZifop-butyl, propaquizafop, quizalo ing plants which comprises applying to the plants or to the fop-P, metamifop, pyriftalid; phenoxys Such as 2,4-D, 2.4.5- locus thereof an effective controlling amount of the com T,2,4-DB, MCPA, silvex, 2,4-DP. MCPB, MCPP; ureas such pounds/compositions of the present invention. as fluometuron, linuron, diuron and monuron, fenuron-TCA, 0107 The compositions of the present invention can be siduron, tebuthiuron, isoproturon, cumyluron; phosphono applied to the soil, plant, seed, or other area to be protected. amino acids such as glyphosate, glufosinate, fosamine and Preferably the present invention is applied to the foliage of glyphosate trimesium; phthalic acid Such as chlorthal, endot plants. The composition may be applied in the form of dusting hall; pyridaZinones such as pyrazon, norflurazon, fluridone, powders, wettable powders, granules (slow or fast release), fluorochloridone, clomaZone, oxadiazon, beflubutamid, water dispersible granules, emulsion or Suspension concen US 2012/0088.667 A1 Apr. 12, 2012

trates, liquid solutions, emulsions, seed dressings, or con dard techniques and through conventional seed treaters. In trolled release formulations such as microencapsulated gran use the compositions are applied to the plants, to the locus of ules or Suspensions, Soil drench, irrigation component, or the plants, by any of the known means of applying fertiliser preferably a foliar spray. compositions, for example, by dusting, spraying, or incorpo 0108 Dusting powders are formulated by mixing the ration of granules. active ingredient with one or more finely divided solid carri 0.115. As indicated above, the composition of the present ers and/or diluents, for example natural clays, kaolin, pyro invention can be applied at the same time as or at an appro phyllite, bentonite, alumina, montmorillonite, kieselguhr, priate interval to the agrochemical. This can be readily deter chalk, diatomaceous earths, calcium phosphates, calcium and mined by a skilled worker, e.g. it may be in the range of 1-3 magnesium carbonates, Sulfur, lime, flours, talc and other days prior to application of the agrochemical. organic and inorganic Solid carriers. 0116. As indicated above, the compositions according to 0109 Granules are formed either by absorbing the active this present invention may be applied to the foliage of plants ingredient in a porous granular material for example pumice, but may also be applied to the soil or added to the irrigation attapulgite clays, fuller's earth, kieselguhr, diatomaceous Water. earths, ground corn cobs, and the like, or on to hard core 0117 The present invention is useful in relation to crops. It materials such as sands, silicates, mineral carbonates, Sul will be appreciated that the present invention may be appli fates, phosphates, or the like. Agents which are commonly cable to all horticultural and agricultural species. used to aid in impregnation, binding or coating the Solid 0118. The present invention is useful in relation to fruit carriers include aliphatic and aromatic petroleum solvents, crops. The crops can include trees, bushes, shrubs and vines. alcohols, polyvinyl acetates, polyvinyl alcohols, ethers, 0119 The present invention is useful in relation to veg ketones, esters, dextrins, Sugars and vegetable oils, with the etable crops. active ingredient. Other additives may also be included, such 0.120. The present invention is useful in relation to agri as emulsifying agents, wetting agents or dispersing agents. cultural and horticultural crops including ornamentals. 0110 Microencapsulated formulations (microcapsule I0121 The present invention is useful in relation to cereals Suspensions CS) or other controlled release formulations may and grasses and to pod-bearing, bean and oilseed crops. also be used, particularly for slow release over a period of 0.122 Particularly, but not exclusively, when the present time, and for seed treatment. invention is used in combination with a chemical thinner the 0111 Alternatively and preferred the compositions may present invention is useful in relation to fruit crops. The crops be in the form of liquid preparations to be used as dips, can include trees, bushes, and vines. irrigation additives or sprays, which are generally aqueous I0123 Particularly, but not exclusively, when the present dispersions or emulsions of the active ingredient in the pres invention is used in combination with cobalt the present ence of one or more known wetting agents, dispersing agents invention is useful in relation to nitrogen-fixing crops. The or emulsifying agents (surface active agents). The composi nitrogen-fixing crops can include Soybean, navy bean and tions which are to be used in the form of aqueous dispersions pea. or emulsions are generally Supplied in the form of an emul 0.124. The present invention can be used on the following sifiable concentrate (EC) or a suspension concentrate (SC) plants as non-limiting examples: Almond (Prunus dulcis), containing a high proportion of the active ingredient or ingre Apple (Malus domestica), Apricot (Prunus armeniaca), Avo dients. An EC is an homogeneous liquid composition, usually cado (Persea americana), Banana, Plantain (Musa spp.), containing the active ingredient dissolved in a Substantially Blackberries (Rubus spp), Blueberries (Vaccinium spp). non-volatile organic solvent. An SC is a fine particle size Cacao or cocoa (Theobroma cacao), Cashew (Anacardium dispersion of Solid active ingredient in water. To apply the occidentale), Chemies (Prunus cerasus, Pavium), Chestnuts concentrates they are diluted in water and are usually applied (Castanea spp.), Coconut (Cocos nucifera), Coffee (Coffea by means of a spray to the area to be treated. arabica, C. canephora), Cranberry (Vaccinium macrocar 0112 Suitable liquid solvents for ECs include methyl pon), Currants (Ribes spp). Date (Phoenix dactylifera), Fig ketone, methyl isobutyl ketone, cyclohexanone, Xylenes, (Ficus carica), Gooseberry (Ribes grossularia, R. hirtellum), toluene, chlorobenzene, paraffins, kerosene, white oil, alco Grapefruit (Citrus paradisi), Grapes (Vitis vinifera, other hols (for example, butanol), methylnaphthalene, trimethyl Vitis spp), Guava (Psidium guajava & related spp), Hazelnut benzene, trichloroethylene, N-methyl-2-pyrrolidone and tet or filbert (Corylus avellana), Juneberry (Amelanchier alnifo rahydrofurfuryl alcohol (THFA). lia), Kiwifruit (Actinidia deliciosa), Kumquat (Fortunella 0113. These concentrates are often required to withstand spp), Lemon (Citrus limon), Lime (Citrus aurantifolia), storage for prolonged periods and after Such storage, to be Loquat (Eriobotrya japonica), Macadamia (Macadamia capable of dilution with water to form aqueous preparations integrifolia), Mango (Mangifera indica), Mayhaw (Cratae which remain homogeneous for a sufficient time to enable gus spp.), Oil Palm (Elaeis guineensis), Olive (Olea euro them to be applied by conventional spray equipment. The paea), Orange (Citrus sinensis), Papaya (Carica papaya), concentrates may contain 1-85% by weight of the active Peach (Prunus persica), Pears (Pyrus communis, P. pyrifo ingredient or ingredients. When diluted to form aqueous lia), Pecan (Carya illinoensis), Pineapple (Ananas comosus), preparations such preparations may contain varying amounts Pistachio (Pistacia vera), Plums (Prunus domestica, P. of the active ingredient depending upon the purpose for which salicina), Pomegranate (Punica granatum), Quince (Cyclo they are to be used. nia Oblonga), Raspberries (Rubus idaeus, R. Occidentalis), 0114. The composition may also be formulated as pow Strawberry (Fragaria Xananassa), Tangerine (Citrus reticu ders (dry seed treatment DS or water dispersible powder WS) lata), Walnut (Juglans regia Chrysanthemum, and Rhododen or liquids (flowable concentrate FS, liquid seed treatment dron including Azalea species (e.g. Azaleastrum), Kalan LS), or microcapsule Suspensions CS for use in seed treat choe, Bulb crops, Crocus, Tulip, Narcissus, Hyacinth, ments. The formulations can be applied to the seed by stan Poinsettia and Roses, tomatoes, squash, pumpkin, beans, US 2012/0088.667 A1 Apr. 12, 2012 broccoli, greenbeans, asparagus, peas, corn, carrots, spinach, events). For example, seed can have the ability to express an cauliflower, lima beans, broad beans, french beans, runner insecticidal Cry3 protein while at the same time being toler beans, navy beans, kidney beans, lentils, cabbage, onions, ant to glyphosate. courgettes, aubergines, Sweet basil, leeks, artichokes, lettuce, I0129. The addition of the following mixtures of the com cassaya leaves, tomatoes, cucumbers and gherkins, marrows, pounds of the present invention are particularly mentioned: gourds, squashes, chillies and peppers, green onions, dry 1. The addition of Anthranilic acid (AN). onions, red onions, shallots, garlic, chives, other alliaceous 2. The addition of NAA/other auxins, or auxin mixes (eg Vegetables, okra, mushrooms, watermelons, cantaloupe mel NAA/BA). ons, other melons, bamboo shoots, beets, chards, capers, car 3. The addition of a safener (SAF). doons, celery, chervil, cress, fennel, horseradish, marjoram, 4. The addition of Anthranilic acid (AN) to a safener (SAF). oyster plant, parsley, parsnips, potato, radish, rhubarb, ruta 5. The addition of SAF to NAA/other auxins, or auxin mixes baga, Savory, scorZonera, Sorrel, sprouts, Swede, turnip, (eg NAA/BA). watercress and other vegetables, Maize, wheat, rye, oat, triti 6. The addition of SAF to AN-AC. cale, rice, barley, Sorghum, millet, buckwheat, fonio, quinoa, 7. The addition of SAF to AC+NAA/other auxins, or auxin spelt, other cereal crops, soybean, peanut, cotton, oilseed mixes (eg NAA/BA). rape, Sugar cane, bamboo, Sesame, jute, canola, coconut, 8. The addition to AN to AC. manihot, Sunflower, tobacco, ground nuts, peanuts, oil palm, 9. The addition of AC to NAA/other auxins, or auxin mixes hemp, flax, lucerne, alfalfa tea, perennial grass. (eg NAA/BA). 0.125 Particularly, but not exclusively, when the present 0.130. These combinations and others in accordance with invention is used in combination with a herbicide crops of the present invention may give rise to an additive or synergis useful plants in which the composition according to the tic effect. invention can be used include cereals, for example barley and I0131 The safener (SAF) may be one set out as in classes wheat, cotton, oilseed rape, maize, rice, soybeans, Sugar beet (a) to (f) above. Two or more such additives in the same or and Sugar cane, especially cereals and maize. Crops can also different classes may be used. include trees, such as palm trees, coconut trees or other nuts, 0.132. When the additive is selected from class (a) it is and vines Such as grapes. preferably one or more of glucose, Sucrose, fructose or glyc 0126 The grasses and weeds to be controlled may be both erol. monocotyledonous species, for example Agrostis, Alopecu 0.133 When the additive is selected from class (b) it is rus, Avena, Bromus, Cyperus, Digitaria, Echinochloa, preferably one or more of citric or succinic acid. Lolium, Monochoria, Rottboelia, Sagittaria, Scirpus, I0134. When the additive is selected from class (c) it is Setaria, Sida and Sorghum, and dicotyledonous species, for preferably one or more of thiamine, riboflavin, pyridoxine, example Abutilon, Amaranthus, Chenopodium, Chrysanthe nicotinamide, folic acid, ascorbic acid, biotin or vitamin B12. mum, Galium, Ipomoea, Nasturtium, Sinapis, Solanum, Stel I0135 When the additive is selected from class (d) it is laria, Veronica, Viola and Xanthium. preferably adenine, thymidine, cytosine or uracil. 0127 Crops are to be understood as also including those 0.136. When the additive is selected from class (e) it is crops which have been rendered tolerant to herbicides or preferably a corn oil. classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and 0.137 When the additive is selected from an amino acid (f) HPPD-inhibitors) by conventional methods of breeding or by is it preferably one of more of glycine, alanine, Valine, leu genetic engineering. An example of a crop that has been cine, threonine, cysteine, methionine, glutamine, asparagine rendered tolerant to imidazolinones, e.g. imaZamox, by con or lysine. ventional methods of breeding is ClearfieldR) summer rape 0.138. The following Examples further illustrate, but do (canola). Examples of crops that have been rendered tolerant not limit, the invention. to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties com EXPERIMENTAL RESULTS mercially available under the trade names RoundupReady(R) and LibertyLink R. Example 1 0128. Crops are also to be understood as being those Safening of Fertilisers which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant 0.139 Safening systems were applied to crops of winter to European corn borer), Bt cotton (resistant to cotton boll barley, winter wheat and lettuce treated with various fertiliz weevil) and also Bt potatoes (resistant to Colorado beetle). ers (Potassium Phosphite, potassium phosphite+ammonium Examples of Bt maize are the Bt 176 maize hybrids of NKR) thiosulphate, general NPK fertiliser). The safening system (Syngenta Seeds). The Bt toxin is a protein that is formed and the fertilizer were applied either simultaneously or naturally by Bacillus thuringiensis soil bacteria. Examples of sequentially. toxins, or transgenic plants able to synthesise Such toxins, are Winter Barley: cv Saffron, sown 27 May 2008, at four/five described in EP-A-451878, EP-A-374 753, WO 93/07278, seeds per 9 cm pot, Sown in standard multi-purpose compost WO95/34656, WO 03/052073 and EP-A-427 529. Examples of pH 6.5. Date of spraying: 23 July; Dates of measurement/ of transgenic plants comprising one or more genes that code scoring: 30 July, 14 August, 22 August. Sprayed: mid-tiller for an insecticidal resistance and express one or more toxins ing phase (GS23). are KnockCut(R) (maize), Yield Gard(R) (maize), Winter Wheat: cv Limerick, sown 4 Jun. 2008, at four/five NuCOTIN33B(R) (cotton), Bollgard R. (cotton), NewLeafR) seeds per 9 cm pot, Sown in standard multi-purpose compost (potatoes), NatureGarder) and ProtexctaR). Plant crops or seed of pH 6.5. Date of spraying: 23 July; Dates of measurement/ material thereof can be both resistant to herbicides and, at the scoring: 30 July, 14 August, 23 August. Sprayed: mid-tiller same time, resistant to insect feeding ('stacked' transgenic ing phase (GS23). US 2012/0088 667 A1 Apr. 12, 2012

Lettuce: cv Set, sown 10 Jul. 2008, at one seed perpot, in John Innes No 1 compost. Date of spraying: 30 July; Dates of TABLE 1.1-continued measurement: 7 August, 14 August, 28 August. Sprayed: 2 true leaf stage. WINTER BARLEY - CROP SAFENING BENEFITS FROM SAF: at least one from class (f) each at <3 g/1, plus at least one ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR from class (c). ACETAMINOPEHEN TO APHOSPHITEFERTILISER 0140. The results are shown in Tables 1.1 to 1.9 below. Phyto- Phyto 0141 Tables 1.1, 1.2 and 1.3 (Winter Barley): toxicity toxicity Vigour (0-9) (0-9) (0-9) (9 = (O = (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days Vigour + Phyto +14 Phyto +28 14 Vigour + 28 17 Px2 + AN 7.0 6.5 7.0 7.0 Days Days Days Days 18 Px3 + AN 6.5 6.5 6.5 7.0 LSD (5%) 1.15 1.28 1.39 1.41 19 Px4 - AN 6.5 6.O 6.5 7.5 Treatment Means 2O 5.5 6.O 6.O 7.0 21 C X 5.5 6.O 5.5 7.0 22 S.O S.O 5.5 7.5 23 S.O 5.5 5.5 7.0 0142 Tables 1.4, 1.5 and 1.6 (Winter Wheat): 24 6.5 6.5 6.5 7.0 25 6.5 6.5 7.0 7.5 26 6.5 6.5 S.O 7.0 27 6.5 6.5 6.5 7.5 Vigour + 28 6.5 6.5 6.O 8.O Phyto +14 Phyto +28 14 Vigour + 28 29 6.O 7.0 6.O 7.5 Days Days Days Days 30 6.5 7.0 6.O 8.O LSD (5%) 1.27 1.33 1.38 140 31 6.O 7.0 6.O 7.0 Treatment Means 32 7.0 7.5 7.0 7.5 33 7.5 8.O 7.0 7.5 34 7.0 7.5 6.5 7.5 35 7.0 7.5 6.5 7.5 0143 Tables 1.7, 1.8 and 1.9 (Lettuce): 36 7.5 7.5 7.0 8.O 37 A. 7.0 7.5 7.0 7.5 38 Px3 - AC - SAF 7.5 7.0 6.5 7.0 39 Px4 - AC----F-- - SSA.SAF 6.O 6.5 6.5 7.5 Vigour + 40 Px122222 ------+ A.A.SA.A.ANACCNA.NC + SAF 7.5 7.5 7.0 8.O Phyto +14 Phyto +28 14 Vigour + 28 41 Px2 + AN - AC - SAF 7.5 7.5 7.0 8.O Days Days Days Days 42 Px3 + AN - AC - SAF 7.5 7.5 7.0 8.O LSD (5%) 140 1.38 1.51 148 43 Px4 + ANAC + SAF 7.5 7.5 7.0 8.O Treatment Means K Px1 fb (followed by) 6.5 6.5 6.5 7.5 A. -- AC after 7 days PX2 fb AN+AC after 7 6.O 6.O 6.5 7.5

TABLE 1.1 Px3 flo AN-AC after 7 6.O 6.O 6.O 7.0 day WINTER BARLEY - CROP SAFENING BENEFITS FROM Px4 fb AN+AC after 7 5.5 6.O 6.5 7.5 ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO APHOSPHITEFERTILISER Px1 ft AN - AC - SA 6.5 6.5 6.O 7.0 After 7 days Phyto- Phyto KPX2 ft AN - AC - SA 7.0 6.O 6.O 7.0 toxicity toxicity Vigour After 7 days (0-9) (0-9) (0-9) (9 = KPx3 fib AN - AC - SA 6.5 6.5 6.5 7.5 (O = (O = Most Vigour After 7 days Dead) + Dead) + Vigour) + (0-9) + KPX4 f5 AN-AC - SA 6.O 6.O 7.0 7.0 Treatment 14 Days 28 Days 14 days 28 Days After 7 days KP x1 ft AN - AC - SA 6.O 7.0 6.O 7.0 1. Untreated 8.0 7.5 8.O 8.O Ter 2. Untreated 7.5 8.0 8.O 8.O pene after 7 days 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.O 53 KPX2 ft AN - AC - SA 6.O 6.5 6.5 7.0 4. AC (Acetaminophen) 8.0 8.0 7.0 8.O Ter pene after 7 days 5. ANAC 7.5 7.5 7.5 8.O S4 KPx3 fib AN - AC - SA 5.5 6.5 7.0 7.5 6. AN + AC + Terpene 7.5 7.5 7.5 8.O Ter pene after 7 days 7. SAF 7.5 7.5 8.O 8.O 55 KPX4 f5 AN-AC - SA 5.5 7.0 7.0 7.5 8. AN - SAF 8.0 8.0 8.O 8.O Ter pene after 7 days 9. AC - SAF 7.5 7.5 8.O 7.5 56 KPX1 fb SAF after 7.0 7.0 7.0 7.5 1 OAN - AC - SAF 8.0 8.0 8.O 8.O 7 days 11 AN + AC + SAF + 8.0 8.0 8.O 8.O 57 KPX2 fb SAF after 7.0 7.0 7.0 7.5 Terpene 7 days 6.5 6.5 7.5 7.5 12 Potassium Phosphite 58 KPX3 fb SAF after 6.5 7.0 7.0 7.0 (KP) - 3.0 l/ha = KPx1 13 KPx2 (4.0 l/ha) 6.5 6.O 7.0 7.5 7 days 14 KPx3 (5.0 l/ha) 6.5 6.O 7.0 7.5 59 KPX4 fb SAF after 5.5 6.5 6.5 7.0 15 KPx4 (6.0 l/ha) 5.5 6.O 6.5 7.0 7 days 16KP x1 + AN 7.0 6.5 7.5 7.5 US 2012/0088.667 A1 Apr. 12, 2012 11

TABLE 1.2 TABLE 1.3-continued

WINTER BARLEY - CROP SAFENING BENEFITS FROM WINTER BARLEY - CROP SAFENING BENEFITS FROM ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO APHOSPHITEFERTILISER ACETAMINOPEHEN TO GENERAL FERTILISERS. Phyto- Phyto Vigour toxicity toxicity Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (0-9) (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour (O = (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days Treatment 14 Days 28 Days 14 days 28 Days 12 Genera 6.O 7.0 7.5 8.0 1. Untreated 8.0 7.5 8.O 8.O 2. Untreated 7.5 8.0 8.O 8.O Fertiliser + 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.O micronutrients 4. AC (Acetaminophen) 8.0 8.0 7.0 8.O with added KP(a) 5. ANAC 7.5 7.5 7.5 8.O x2 rate (4.0 l/ha) = 6. AN + AC + Terpene 7.5 7.5 7.5 8.O GEN - KP x2 7. SAF 7.5 7.5 8.O 8.O 13 GEN 6.O 6.5 7.5 8.0 8. AN - SAF 8.0 8.0 8.O 8.O (6.0 l/ha) 9. AC - SAF 7.5 7.5 8.O 7.5 14 GEN KP x6 5.5 6.0 7.5 8.0 1 OAN - AC - SAF 8.0 8.0 8.O 8.O (12.0 l/ha) 11 AN + AC + SAF + 8.0 8.0 8.O 8.O 1SGEN 6.5 7.0 8.0 8.0 Terpene AN + AC 12 Potassium Phosphite 7.0 7.5 7.0 7.0 16 GEN 6.5 7.0 7.5 8.0 (KP) + Ammonium AN + AC Thiosulphate (ATS) - 4.0 l/ha = 17 GEN KPx6 - 6.O 6.5 8.0 8.0 KPATS x1 AN + AC 13 KP/ATS x2 (6.0 l/ha) 7.0 7.5 7.5 7.0 18 GEN 7.0 7.0 8.0 8.0 14 KP/ATS x3 (8.0 l/ha) 6.5 7.0 7.0 7.5 15 KP/ATS x4 (10.0 l/ha) 6.0 7.0 6.5 7.0 SAF 24 KPFATS x1 + AN+AC 6.0 6.5 7.0 8.O 19 GEN 7.0 7.0 8.0 8.0 25 KPFATS x2 + AN+AC 6.0 6.5 6.5 8.O SAF 26KPFATS x3 + AN+AC 6.0 7.0 6.5 7.5 2O GEN KPx6 - 7.0 7.0 7.0 7.5 27 KPFATSX4+ AN+AC 6.5 7.0 6.5 8.O SAF 28 KPFATS x1 + SAF 7.5 8.0 7.5 8.O 21 GEN 8.0 8.0 8.0 8.0 29 KPFATS x2 + SAF 7.5 8.0 8.O 8.O AN + AC+ 30 KPFATS x3 - SAF 7.5 8.0 7.5 8.O SAF 31 KPFATSX4 + SAF 6.5 7.5 7.0 7.5 22 GEN 8.0 8.0 8.0 8.0 32 KPFATS x1 + AN+AC+ 7.5 8.0 8.O 8.O AN + AC+ SAF SAF 33 KPFATS x2 + AN+AC+ 7.5 7.5 8.O 8.O 23 GEN KPx6 - 7.5 7.5 7.5 7.5 SAF AN + AC+ 34 KPFATS x3 + AN+AC+ 7.5 8.0 8.O 8.O SAF SAF 24 Genera 6.O 7.5 8.0 8.0 35 KPFATSX4+ AN+AC+ 7.0 7.5 7.0 8.O Fertiliser + SAF micronutrients, but with NO added KP GENEX x2 rate TABLE 1.3 25 GE EX x3 6.O 7.5 8.0 8.0 rate WINTER BARLEY - CROP SAFENING BENEFITS FROM 26 GE EXx6 6.O 7.5 6.5 7.5 ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR rate ACETAMINOPEHEN TO GENERAL FERTILISERS. 27 GENEX x2 6.5 7.5 8.0 8.0 AN + AC Vigour 28 GENEX x3 . 6.5 7.5 7.5 8.0 Phytotoxicity Phytotoxicity (0-9) (9 = AN + AC (0-9) (O = Most Vigour 29 GENEX x6 6.5 7.5 7.0 8.0 Dead) + Dead) + Vigour) + (0-9) + AN + AC Treatment 14 Days 28 Days 14 days 28 Days 3O GENEX x2 7.0 7.5 8.0 8.0 1. Untreated 8.0 7.5 8.O 8.0 2. Untreated 7.5 8.O 8.O 8.0 31 GENEX x3 . 7.0 8.0 8.0 8.0 3. AN 7.5 8.O 7.0 8.0 SAF 4. AC 8.0 8.O 7.0 8.0 32 GENEX x6 7.0 7.5 7.5 8.0 5. ANAC 7.5 7.5 7.5 8.0 6. AN+AC + 7.5 7.5 7.5 8.0 33 GENEX x2 8.0 8.0 8.0 8.0 Terpene AN + AC+ SAF 7. SAF 7.5 7.5 8.O 8.0 34 GENEX x3 + 8.0 7.5 8.0 8. AN - SAF 8.0 8.O 8.O 8.0 AN + AC+ 9. AC - SAF 7.5 7.5 8.O 7.5 SAF 10 ANAC + 8.0 8.O 8.O 8.0 3S GENEX x3 . 8.0 8.0 8.0 8.0 SAF ANAC - SAF 11 AN + AC+ 8.0 8.O 8.O 8.0 SAF + Terpene

US 2012/0088.667 A1 Apr. 12, 2012 13

TABLE 1.5-continued TABLE 1.6-continued

WINTER WHEAT - CROP SAFENING BENEFITS FROM WINTER WHEAT - CROP SAFENING BENEFITS FROM ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO THIOSULPHATE AND PHOSPHITE ACETAMINOPEHEN TO GENERAL FERTILISERS. FERTILISERS Vigour Phytotoxicity Phytotoxicity (0-9) (9 = Phyto- Phyto (0-9) (O = (0-9) (O = Most Vigour toxicity toxicity Vigour Dead) + Dead) + Vigour) + (0-9) + (0-9) (0-9) (0-9) (9 = Treatment 14 Days 28 Days 14 days 28 Days (O = (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + 24 General NPK 7.0 8.0 8.0 8.0 Treatment 14 Days 28 Days 14 days 28 Days Fertiliser + micronutrients, but with NO 35 KPFATSX4+ AN+AC+ 7.0 7.0 7.0 7.0 added KP = SAF GENEX x2 rate 2S GENEX x3 7.0 8.0 8.0 8.0 rate 26 GENEX x6 7.0 7.5 6.0 7.0 TABLE 1.6 rate 27 GENEX x2- 7.0 7.5 8.0 8.0 WINTER WHEAT - CROP SAFENING BENEFITS FROM AN + AC ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR 28 GENEX x3 . 7.0 8.0 8.0 8.0 ACETAMINOPEHEN TO GENERAL FERTILISERS. AN + AC 29 GENEX x6- 7.0 7.5 6.5 7.0 Vigour AN + AC Phytotoxicity Phytotoxicity (0-9) (9 = 3O GENEX x2- 7.0 7.0 8.0 8.0 (0-9) (O = (0-9) (O = Most Vigour SAF Dead) + Dead) + Vigour) + (0-9) + 31 GENEX x3 . 6.5 7.0 8.0 8.0 Treatment 14 Days 28 Days 14 days 28 Days SAF 32 GENEX x6- 7.0 7.0 8.0 8.0 1. Untreated 7.5 8.O 8.O 8.0 SAF 2. Untreated 7.0 8.O 8.O 8.0 33 GENEX x2- 7.0 7.5 8.0 8.0 3. AN 7.5 8.O 8.O 8.5 AN + AC+ SAF 4. AC 7.0 8.O 8.O 8.0 34 GENEX x3 + 7.5 8.0 8.0 8.0 5. ANAC 7.0 8.O 8.O 8.0 AN + AC+ 6. AN+AC + 7.0 8.O 8.O 8.0 SAF Terpene 3S GENEX x3 . 7.5 8.0 7.0 8.0 7. SAF 7.0 8.O 8.O 8.0 ANAC - SAF 8. AN - SAF 7.0 8.O 8.5 8.0 9. AC - SAF 7.0 8.O 8.O 8.0 10 ANAC + 7.0 8.O 8.O 8.0 SAF TABLE 1.7 11 AN + AC+ 7.0 8.O 8.O 8.0 SAF + Terpene LETTUCE - CROP SAFENING BENEFITS FROMADDITION OF 12 General NPK 7.0 6.5 8.O 8.0 SAFENER AND, ORANTHRANILIC ACID AND, OR Fertiliser + ACETAMINOPEHEN TO PHOSPHITEFERTILISER micronutrients, with added KP(a) Phyto- Phyto x2 rate (4.0 l/ha) = toxicity toxicity Vigour GEN - KP x2 (0-9) (0-9) (0-9) (9 = 13 GEN - KP x3 6.5 7.0 8.O 8.0 (O = (O = Most Vigour (6.0 l/ha) Dead) + Dead) + Vigour) + (0-9) + 14 GEN - KPx6 7.0 7.5 8.O 8.0 Treatment 14 Days 28 Days 14 days 28 Days (12.0 l/ha) 15 GEN - KPx2 + 6.5 7.0 7.5 8.0 1. Untreated 7.5 7.5 8.O 8.O AN + AC 2. Untreated 7.5 8.O 8.O 8.O 16 GEN - KPx3 + 6.O 7.0 8.O 8.0 3. AN (Anthranilic Acid) 7.0 7.0 8.O 8.O AN + AC 4. AC (Acetaminophen) 7.0 6.5 8.O 8.O 17 GEN - KPx6 - 6.O 7.0 7.5 8.0 5. ANAC 7.0 7.0 7.5 8.O AN + AC 6. AN + AC + Terpene 7.0 7.0 7.5 8.O 18 GEN - KPx2 + 7.0 7.5 8.O 8.0 7. SAF 7.0 7.0 7.5 8.O SAF 8. AN - SAF 7.5 7.5 8.O 8.O 19 GEN - KPx3 + 7.0 7.0 8.O 8.0 9. AC - SAF 7.5 7.5 8.O 8.O SAF 10 ANAC - SAF 7.5 8.O 8.O 8.O 2O GEN - KPx6 - 7.0 7.0 8.O 8.5 11 AN + AC + SAF + 7.5 8.O 8.O 8.O SAF Terpene 21 GEN - KPx2 + 7.0 7.5 8.O 8.5 12 Potassium Phosphite 7.0 7.0 7.5 7.5 AN+AC + (KP) - 2.0 l/ha = KPx1 SAF 13 KPx2 (3.0 l/ha) 7.0 6.5 8.O 8.O 22 GEN - KPx3 + 7.0 7.5 7.5 8.0 14 KPx3 (4.0 l/ha) 7.0 6.5 7.5 7.5 AN+AC + 15 KPx4 (5.0 l/ha) 6.5 6.5 7.0 7.5 SAF 16KP x1 + AN 7.0 7.0 7.0 8.O 23 GEN - KPx6 - 7.0 8.O 7.5 8.5 17. KPX2 - AN 7.0 7.0 7.0 8.O AN+AC + 18. KPX3 - AN 6.5 7.0 7.0 8.O SAF 19 KPx4 - AN 7.0 7.0 8.O 8.O

US 2012/0088.667 A1 Apr. 12, 2012

Maize: cv Sundance, sown 25 May 2008, at 10 seeds per 25 TABLE 1.9-continued cm pot, in John Innes No 1 compost. Date of measurement/ assessment: 15 June. Seed treatment trial. Randomised block, LETTUCE - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR mean of five replicates. ACETAMINOPEHEN TO GENERAL FERTILISERS. Safening Systems: Phyto- Phyto toxicity toxicity Vigour 1. Anthranilic Acid-i-Acetaminophen (AN+AC). (0-9) (0-9) (0-9) (9 = (O = (O = Most Vigour 2. AN+AC+Safener (SAF). Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days 3. Safener (SAF). 13 GEN + KPx3 (6.0 l/ha) S.O S.O 6.5 7.0 0146 SAF: at least one from class (f) each at <3 g/1, plus at 14 GEN + KPx6 (12.0 l/ha) 4.5 4.0 7.0 6.5 least one from class (c). 15 GEN - KPx2 + ANAC 7.0 7.0 7.0 6.5 0147 Statistical Analyses (Least Significant Difference, 16 GEN - KPx3 + ANAC 6.0 6.O 6.5 7.0 17 GEN - KPx6 - ANAC S.O 5.5 6.5 7.0 5% Level) for Tables 2.1 to 2.7: 18 GEN - KPx2 + SAF 7.0 7.0 8.O 8.O 0148 Tables 2.1, 2.2 and 2.3 (Winter Barley): 19 GEN - KPx3 + SAF 6.5 7.0 7.5 7.5 2O GEN - KPx6 - SAF 7.0 6.5 7.5 7.5 21 GEN - KPx2 + AN-AC- 7.5 7.0 8.O 8.O SAF Vigour + 22 GEN - KPx3 + AN-AC- 7.0 7.0 7.5 8.O Phyto + 14 Phyto + 28 14 Vigour + 28 SAF Days Days Days Days 23 GEN - KPx6 - AN-AC- 7.0 7.0 8.O 8.O SAF LSD (5%) 1.15 1.28 1.39 1.41 24 General NPKFertiliser- 7.5 7.5 8.O 8.O Treatment Means micronutrients, but with NO added KP = GENEXX2 rate 25 GENEX x3 rate 6.0 6.5 7.0 7.5 26 GENEX x6 rate 4.5 S.O 7.0 8.O 0149 Tables 2.4, 2.5 and 2.6 (Winter Wheat): 27 GENEX x2 + ANAC 7.5 7.0 8.O 8.O 28 GENEX x3 + ANAC 6.5 7.0 7.0 8.O 29 GENEX x6 - ANAC S.O 6.O 7.0 7.5 3 O GENEX x2 - SAF 7.0 7.5 8.O 8.O Vigour + 31 GENEX x3 - SAF 7.0 7.0 8.O 8.O Phyto + 14 Phyto + 28 14 Vigour + 28 32 GENEX x6 - SAF 6.5 7.0 8.O 8.O Days Days Days Days GENEX x2 + AN-AC- 7.0 7.5 8.O 8.O SAF LSD (5%) 1.27 1.33 1.38 140 GENEX x3 + AN-AC- 7.0 7.0 8.O 8.O Treatment Means SAF GENEX x3 + ANAC - SAF 7.0 7.5 7.0 8.O O150 Table 2.7 (Maize): 0144. As shown in Tables 1.1 to 1.9, each of the safening formulations showed a significant reduction in phytotoxicity when applied to a range of species in combination with a Shoot Fresh Vigour fertilizer, when compared to the application of fertilizers Weight (g) % (0-9) alone. Thus the Safening systems improve crop safening in a LSD (5%) 2.30 9.6 1.51 range of species. Vigour was also boosted. Treatment Means

Example 2 0151. The results are shown in Tables 2.1 to 2.7 below.

Safening of Fungicides TABLE 2.1

0145 Safening systems were applied to crops of winter WINTER BARLEY - CROP SAFENING BENEFITS FROM barley, winter wheat and maize treated with various fungi ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR cides (Prochloraz, Flutriafol, Fenpropidin). The safening sys ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ. tem and the fungicide were applied to the crops either simul Phyto- Phyto- Vigour taneously or sequentially, either as foliar applications or as a toxicity toxicity (0-9) (9 = seed treatment. (0-9) (O = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Winter Barley: cv Saffron, sown 27 May 2008, at four/five Treatment 14 Days 28 Days 14 days 28 Days seeds per 9 cm pot, Sown in standard multi-purpose compost 1. Untreated 8.O 7.5 8.O 8.O of pH 6.5. Date of spraying: 23 July; Dates of measurement/ 2. Untreated 7.5 8.0 8.O 8.O scoring: 30 July, 14 August, 22 August. Sprayed: mid-tiller 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.O ing phase (GS23). 4. AC (Acetaminophen) 8.O 8.0 7.0 8.O Winter Wheat: cv Limerick, sown 4 Jun. 2008, at four/five 5. ANAC 7.5 7.5 7.5 8.O 6. AN + AC + Terpene 7.5 8.0 7.5 8.O seeds per 9 cm pot, Sown in standard multi-purpose compost 7. SAF 7.5 8.0 7.5 8.O of pH 6.5. Date of spraying: 23 July; Dates of measurement/ 8. AN - SAF 8.O 8.0 8.O 8.O scoring: 30 July, 14 August, 23 August. Sprayed: mid-tiller 9. AC - SAF 7.5 7.5 8.O 7.5 ing phase (GS23). US 2012/0088.667 A1 Apr. 12, 2012 16

TABLE 2.1-continued TABLE 2.1-continued

WINTER BARLEY - CROP SAFENING BENEFITS FROM WINTER BARLEY - CROP SAFENING BENEFITS FROM ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ. ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ. Phyto Phyto Vigour Phyto Phyto- Vigour toxicity toxicity (0-9) (9 = toxicity toxicity (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour (0-9) (O = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days Treatment 14 Days 28 Days 14 days 28 Days OAN - AC - SAF 8.O 8.0 8.O 8.O 39 PRO x1 - SAF - POL 7.5 8.0 8.O 8.O 1 ANAC + SAF + 8.O 8.0 8.O 8.O 4O PRO x2 + SAF - POL 7.5 8.0 7.0 8.O erpene 41 PROx3- SAF- 7.0 7.5 7.0 7.5 2 ProchloraZ (400 g/l)(a) 6.5 7.0 7.0 7.0 POL 0.75 ha = PROX1 42 PRO x1 fb (followed by) 6.5 7.0 7.0 7.5 3 PRO (a) 1.25 l/ha = 6.5 7.0 6.5 7.0 AN + AC after 7 days PRO x2 43 PRO x2 fib ANAC 6.5 7.0 7.0 7.5 4PRO (a) 1.75 l/ha = 6.O 7.0 6.5 7.0 after 7 days PRO x3 44 PRO x3 fib ANAC 6.O 7.0 6.5 7.0 RO x1 + AN 6.5 7.0 7.0 7.0 after 7 days RO x2 + AN 6.O 7.0 6.O 7.0 45 PROX1 fbAN after 6.O 7.0 7.0 7.5 RO x3 + AN 6.O 6.5 6.O 6.5 7 days RO x1 + AC 6.O 6.5 6.5 7.0 46 PROx2 fbAN after 6.5 7.0 6.O 7.0 RO x2 + AC 6.O 6.5 6.O 6.5 7 days RO x3 + AC 6.O 6.5 6.O 6.O 47 PRO x3 f AN after 6.O 6.5 6.O 7.0 RO x1 + ANAC 7.0 8.0 7.5 7.0 7 days RO x2 + ANAC 7.0 7.0 7.0 7.0 48 PRO x1 fib AN-AC- 7.0 7.0 7.5 8.O RO x3 + ANAC 6.5 7.0 7.0 7.0 SAF after 7 days RO x1 - SAF 7.0 8.0 8.O 8.O 49 PRO x2 fib AN-AC- 6.5 7.0 7.5 8.O 2 5 RO x2 + SAF 7.0 7.5 7.5 8.O SAF after 7 days RO x3 + SAF 7.0 7.0 7.5 8.O SO PRO x3 fib AN-AC- 6.O 7.0 6.5 7.0 RO x1 + AN - SAF 7.0 7.0 8.O 8.O SAF after 7 days RO x2 + AN - SAF 7.0 7.0 7.0 7.5 51 PRO x1 ft AN-AC- 7.0 6.O 7.5 8.O RO x3 + AN - SAF 7.0 7.0 7.0 7.5 SAF + POL after 7 days RO x1 + ANAC + 7.0 7.0 8.O 8.O 52 PRO x2 ft AN-AC- 7.0 7.0 6.O 7.0 SAF + POL after 7 days RO x2 + ANAC + 7.0 7.5 7.0 7.5 53 PRO x3 fib AN-AC- 6.O 7.0 6.O 6.5 SAF + POL after 7 days RO x3 + ANAC + 7.5 7.0 7.5 7.5 S4 PRO x1 ft SAF after 7 6.5 7.0 7.5 7.5 days RO x1 + ANAC + 6.5 7.5 7.0 7.5 SS PRO x2 ft SAF after 7 6.5 7.0 7.5 8.O p RO x2 + ANAC + 7.0 7.5 7.0 7.0 days S6 PRO x3 ft SAF after 7 6.O 7.0 7.5 7.5 pg d RO x3 + ANAC + 6.5 7.5 6.5 7.0 days S7 PRO x1 ft AN-SAF 7.0 7.0 8.O 7.5 RO x1 + ANAC + 7.0 7.5 7.5 8.O after 7 days - POL S8 PRO x2 ft AN-SAF 6.O 6.5 7.5 8.O 3 7 RO x2 + ANAC + 7.0 8.0 7.0 7.5 after 7 days - POL S9 PRO x3 f AN-SAF 6.O 7.0 7.0 7.0 RO x3 + ANAC + 7.0 7.5 7.0 7.0 after 7 days - POL

TABLE 2.2

WINTERBARLEY - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE FUNGICIDE FLUTRLAFOL. Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days

1. Untreated 8.O 7.5 8.0 8.0 2. Untreated 7.5 8.0 8.0 8.0 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.0 4. AC (Acetaminophen) 8.O 8.0 7.0 8.0 5. ANAC 7.5 7.5 7.5 8.0 6. AN + AC + Terpene 7.5 8.0 7.5 8.0 7. SAF 7.5 8.0 7.5 8.0 8. AN - SAF 8.O 8.0 8.0 8.0

US 2012/0088.667 A1 Apr. 12, 2012 18

TABLE 2.2-continued

WINTER BARLEY - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, ORACETAMINOPHEN TO THE FUNGICIDE FLUTRLAFOL. Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days S4 FLUX1 ft SAF after 7 5.5 7.0 7.0 8.0 days SS FLU x2 ft SAF after 7 5.5 6.5 6.5 7.5 days S6 FLU x3 ft SAF after 7 5.5 6.5 6.5 7.0 days 57 FLUX1 ft AN - SAF 6.O 7.0 7.0 8.0 after 7 days S8 FLU x2 ft AN - SAF 6.O 7.0 6.0 7.0 after 7 days S9 FLU x3 f AN-SAF 5.5 6.5 6.0 7.0 after 7 days

TABLE 2.3

WINTER BARLEY - CROP SAFENING BENEFITS FROM ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO THE FUNGICIDES FENPROPIDIN AND FLUTRLAFOL. Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour Dead) + 14 Dead) + Vigour) + (0-9) + Treatment Days 28 Days 14 days 28 Days 1. Untreated 8.O 7.5 8.0 8.0 2. Untreated 7.5 8.0 8.0 8.0 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.0 4. AC (Acetaminophen) 8.O 8.0 7.0 8.0 5. ANAC 7.5 7.5 7.5 8.0 6. AN + AC + Terpene 7.5 8.0 7.5 8.0 7. SAF 7.5 8.0 7.5 8.0 8. AN - SAF 8.O 8.0 8.0 8.0 9. AC - SAF 7.5 7.5 8.0 7.5 1 OAN - AC - SAF 8.O 8.0 8.0 8.0 11 AN + AC + SAF + 8.O 8.0 8.0 8.0 Terpene 12 Fenpropidin (750 g/l)(a) 4.0 6.O 7.5 7.0 0.75 l/ha + Flutriafol (125 g/l) (a) 0.75 l/ha = FE + FL x1 13 FE (a 1.0 l/ha + FL (a) 1.0 l/ha = 4.0 6.O 6.0 6.5 FE + FL x2 14 FE (a) 1.3 l/ha + FL (a) 1.3 L/ha = 3.5 5.5 6.0 6.5 FE + FL x3 15 FE + FL x1 + AN 4.0 6.O 7.5 7.0 16 FE + FL x2 + AN 4.0 6.O 7.0 7.0 17 FE + FL x3 + AN 3.5 6.O 6.0 6.O 18 FE + FL x1 - AC 4.0 6.O 7.5 7.0 19 FE + FL x2 + AC 4.0 6.O 6.5 6.5 2OFE + FL x3 + AC 4.0 5.5 6.0 6.5 21 FE + FL x1 + ANAC 4.5 6.5 7.5 7.5 22 FE-FL x2 + ANAC 4.0 6.O 7.0 7.0 23 FE-FL x3 + ANAC 4.0 6.O 6.5 7.0 24 FE-FL x1 - SAF 6.5 7.0 7.5 8.0 25 FE-FL x2 + SAF 6.5 7.0 7.5 8.0 26 FE-FL x3 + SAF 5.5 6.O 7.5 7.5 27 FE-FL x1 - AN - SAF 6.5 7.0 8.0 7.5 28 FE-FL x2 + AN - SAF 6.5 6.5 7.5 7.5 29 FE-FL x3 + AN - SAF 5.5 6.5 7.5 7.5 30FE + FL x1 + AN+AC + 6.O 7.0 8.0 7.5 SAF 31FE + FL x2 + AN+AC + 6.O 7.0 7.0 7.0 SAF

US 2012/0088.667 A1 Apr. 12, 2012 20

TABLE 2.4-continued TABLE 2.4-continued

WINTER WHEAT - CROP SAFENING BENEFITS FROM WINTER WHEAT - CROP SAFENING BENEFITS FROM ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, OR ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ. ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ. Phyto Phyto Vigour Phyto Phyto- Vigour toxicity toxicity (0-9) (9 = toxicity toxicity (0-9) (9 = Most Vigour (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days Treatment 14 Days 28 Days 14 days 28 Days

45 PROX1 fbAN after 6.5 7.0 8.O 8.O 53 PROX3 fb AN+AC+ S.O 6.O 8.O 8.O 7 days SAF + POL after 7 days 46 PROx2 fbAN after S.O 5.5 7.5 8.O S4 PRO x1 ft SAF after 7 7.5 7.0 7.5 8.O 7 days days 47 PROx3 flo AN after S.O S.O 7.5 8.O SS PRO x2 ft SAF after 7 5.5 6.O 8.O 8.O 7 days days 48 PROX1 fb AN+AC+ 6.5 7.0 8.O 8.O SAF after 7 days S6 PRO x3 ft SAF after 7 4.5 6.O 8.O 8.O 49 PROx2 fb AN+AC+ S.O 5.5 8.O 8.O days SAF after 7 days S7 PRO x1 ft AN-SAF 6.5 7.0 7.5 8.O SOPROX3 fb AN+AC+ 4.5 5.5 8.O 7.5 after 7 days SAF after 7 days S8 PRO x2 ft AN-SAF 7.0 6.O 7.5 8.O 51 PROX1 fb AN+AC+ 7.0 7.0 8.O 8.O after 7 days SAF + POL after 7 days S9 PRO x3 f AN-SAF S.O 5.5 7.5 8.O 52 PRO X2 fb AN+AC+ 5.5 6.O 8.O 8.5 after 7 days SAF + POL after 7 days

TABLE 2.5

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE FUNGICIDE FLUTRLAFOL. Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days

1. Untreated 8.O 7.5 8.0 8.0 2. Untreated 7.5 8.0 8.0 8.0 3. AN (Anthranilic Acid) 7.5 8.0 7.0 8.0 4. AC (Acetaminophen) 8.O 8.0 7.0 8.0 5. ANAC 7.5 7.5 7.5 8.0 6. AN + AC + Terpene 7.5 8.0 7.5 8.0 7. SAF 7.5 8.0 7.5 8.0 8. AN - SAF 8.O 8.0 8.0 8.0 9. AC - SAF 7.5 7.5 8.0 7.5 1 OAN - AC - SAF 8.O 8.0 8.0 8.0 11 AN + AC + SAF + 7.5 8.0 7.5 8.0 Terpene 12 Flutriafol (125 g/l)(a) 0.75 l/ha = 7.0 7.0 8.0 8.0 FLUX1 13 FLU (a 1.25 l/ha = FLU x2 7.0 8.0 7.0 7.0 14 FLU (a) 2.0 l/ha = FLUX3 6.5 7.0 6.5 7.0 15 FLU x1 + AN 6.5 7.0 7.5 7.0 16 FLU x2 + AN 7.0 7.0 7.0 7.0 17 FLU x3 + AN 6.5 7.0 6.5 6.5 18 FLU x1 - AC 7.0 7.0 8.0 8.0 19 FLU x2 + AC 7.0 7.0 7.0 7.0 2O FLU x3 + AC 6.5 7.0 6.5 7.0 21 FLUX1 + AN+AC 7.0 7.0 7.0 7.5 22 FLU x2 + ANAC 6.O 6.5 6.5 6.5 23 FLU x3 + ANAC 6.O 7.0 6.5 7.0 24 FLU x1 - SAF 7.0 7.0 8.0 8.0 25 FLU x2 + SAF 7.0 7.5 8.0 8.0 26 FLU x3 + SAF 7.0 7.0 7.0 7.0 27 FLU x1 + AN-SAF 7.0 7.0 8.0 8.0 28 FLU x2 + AN-SAF 7.0 7.5 6.5 7.0 29 FLU x3 + AN-SAF 7.0 7.0 6.0 6.5 3OFLU x1 + AN - AC - SAF 7.5 7.0 8.0 8.0 US 2012/0088.667 A1 Apr. 12, 2012 21

TABLE 2.5-continued

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, ORANTHRANILIC ACID AND, ORACETAMINOPHEN TO THE FUNGICIDE FLUTRLAFOL.

Vigour Phytotoxicity Phytotoxicity (0-9) (9 = (0-9) (O = (0-9) (O = Most Vigour Dead) + Dead) + Vigour) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days

31 FLU x2 + AN - AC - SAF 7.0 7.0 8.0 8.0 32 FLUX3 + ANAC + 7.0 7.0 8.0 8.0 SA 33 FLUX1 + ANAC + 7.0 7.0 7.0 7.5 POL 34FLU x2 + ANAC + 6.O 6.5 7.0 7.5 POL 35 FLU x3 + AN-AC 6.5 6.5 6.0 6.5 POL 36 FLUX1 + ANAC + SAF + 7.0 7.5 8.0 8.0 POL 37 FLU x2 + AN-AC 7.0 7.0 8.0 7.5 SAF - POL 38 FLU x3 + AN - AC - SAF 7.0 7.0 7.5 7.5 POL 39 FLU x1 - SAF - POL 7.5 7.0 8.0 8.0 40 FLU x2 + SAF - POL 7.0 7.0 8.0 8.0 41 FLU x3 + SAF + 7.0 7.0 7.5 8.0 POL 42 FLU x1 fb (followed by) 7.0 7.5 8.0 8.0 AN + AC after 7 days 43 FLUX2 fb AN+AC after 6.O 6.5 7.0 7.0 7 days 44 FLUX3 fb AN+AC after 6.O 6.5 7.0 6.5 7 days 45 FLU x1 fb AN after 7 days 7.0 7.0 7.0 6.5 46 FLU x2 fb AN after 7 days 7.0 7.0 7.0 6.5 47 FLU x3 fb AN after 7 days 7.0 7.0 6.5 6.5 48 FLUX1 fib AN-AC 7.0 7.0 8.0 7.0 SAF after 7 days 49 FLUX2 fib AN-AC 7.0 7.0 7.0 6.5 SAF after 7 days SOFLU x3 fib AN-AC 6.5 7.0 6.0 6.O SAF after 7 days 51 FLUX1 ft AN - AC 6.5 6.5 7.5 7.5 SAF + POL after 7 days 52 FLU x2 ft AN - AC 7.0 7.0 7.0 7.5 SAF + POL after 7 days 53 FLU x3 fib AN-AC 7.0 7.0 7.0 7.0 SAF + POL after 7 days S4 FLUX1 ft SAF after 7 7.0 6.5 8.0 8.0 days SS FLU x2 ft SAF after 7 6.5 6.5 7.0 7.0 days S6 FLU x3 ft SAF after 7 6.5 6.5 6.5 7.0 days 57 FLUX1 ft AN - SAF 7.0 7.0 8.0 8.0 after 7 days S8 FLU x2 ft AN - SAF 6.5 6.5 7.0 7.5 after 7 days S9 FLU x3 f AN-SAF 6.O 7.0 6.5 7.0 after 7 days

US 2012/0088.667 A1 Apr. 12, 2012 23

TABLE 2.7

MAIZE - BENEFITS TO CROP SAFENING-VIGOURAND EARLY SHOOT FRESHWEIGHT 21 DAYS AFTER SOWING FROMADDITION OF SAFENERPLUS ANTHRANILIC ACID PLUS ACETAMINOPEHEN TO THE FUNGICIDE PROCEHLORAZ WHEN APPLIED AS A SEED TREATMENT.

Percent (%) of Ontreated Control (% of relevant Vigour (0-9); Shoot Fresh Fungicide 9 = most Treatment Rate(s) Weight (g) Control) vigour.

1. Untreated 9.0 1OO 3.9 2. ProchloraZ (400 g/I) 50 ml per 100 kg 3.2 46 (100) S.O x1 See seed Treatment Rate 3. ProchloraZ (400 g/l) 100 ml per 4.8 64 (100) 6.1 x2 Rate 100 kg seed 4. ProchloraZ (400 g/l) 150 ml per 5.9 77 (100) 7.3 x3 Rate 100 kg seed 5. ProchloraZ (400 g/I) 50 ml per 100 kg 5.5 72 (117) 7.4 x1 Rate + AN+ seed +3 ml AC - SAF per 500 g seed 6. ProchloraZ (400 g/l) 100 ml per 7.8 98 (120) 7.8 x2 Rate + AN+ 100 kg seed + AC - SAF 3 ml per 500 g seed 7. Prochloraz (400 g/l) 150 ml per 6.4 82 (103) 7.5 x3 Rate + AN+ 100 kg seed + AC - SAF 3 ml per 500 g seed

0152. As shown in Tables 2.1 to 2.7, each of the safening Statistical Layout: Randomised Complete Block trials, under formulations showed a significant reduction in phytotoxicity glasshouse conditions, United Kingdom. when applied to a range of species in combination with fun gicides, when compared to the application of fungicides 0155 Statistical Analyses (Least Significant Difference, alone. Thus the Safening systems improve crop safening in a 5% Level) for Tables 3.1 to 3.5: range of species. This applies to either the safening formula 0156 Tables 3.1 and 3.2: tions applied in foliar applications (Tables 2.1 to 2.6) or as seed treatments (Table 2.7). Increases in vigour and early shoot weight are also noted. Example 3 Green- Green LSD (5%) Phyto + Phyto + Vigour + Vigour + ness + ness + Safening of Herbicides Treatment 14 28 14 28 14 28 0153. Safening systems were applied to crops of oilseed Means Days Days Days Days Days Days rape and winter treated with various herbicides (Bilfenox (with insecticide), Carbetamide, Propaquizafop, Chlorotolu 122 1.31 1.44 1.37 1.35 1.36 ron, Isoproturon, Flumioxazin). The Safening system and the herbicide were applied to the crops either simultaneously or sequentially. O157 Tables 3.3, 3.4 and 3.5: Oilseed rape: cv Excalibur, sown 26 Apr. 2008, at two seeds per 9 cm pot, Sown in normal pH multi-purpose compost. Date of spraying: 6 June; Dates of measurement/scoring: 13 June, 20 June, 5 July. Green- Green Winter wheat: cv Alchemy, sown 23 Apr. 2008, at seven seeds LSD (5%) Phyto + Phyto + Vigour + Vigour + ness + ness + per 9 cm pot, Sown in normal pH multi-purpose compost. Treatment 14 28 14 28 14 28 Date of spraying: 24 May; Dates of measurement/scoring: 31 Means Days Days Days Days Days Days May, 7 June, 21 June. SAF: at least one from class (f) each at <3 g/1, plus at least one 1.19 1.28 1.47 1.42 1.32 1.37 from class (c). 0154 The results are shown in Tables 3.1 to 3.5 below.

US 2012/0088.667 A1 Apr. 12, 2012 28

TABLE 3.3-continued

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENING SYSTEMAND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE CHLOROTOLURON Phytotoxicity Vigour Greenness (0-9) (O = Phytotoxicity (0-9) (9 = Most Vigour (0-9) (9 = Deeper Greenness Dead) + (0-9) + Vigour) + (0-9) + Green) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days 14 Days 28 Days

51 x2 Chlorfb AN+AC+ SAF + 7.0 6.O 6.5 S.O 8.0 8.0 Terpene after 7 Days 52. X3 Chlorfb AN+AC+ SAF + 7.0 6.O 7.0 S.O 8.0 7.5 Terpene after 7 Days 53. x1 Chlorfb SAF after 6.5 6.O 7.0 6.O 7.0 7.5 7 Days 54. x2 Chlorfb SAF after 6.5 5.5 7.0 6.O 8.0 8.0 7 Days 55. x3 Chlorfb SAF after 6.5 6.O 6.5 5.5 8.0 7.0 7 Days

TABLE 34

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENING SYSTEMAND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE ISOPROTURON Phytotoxicity Vigour Greenness (0-9) (O = Phytotoxicity (0-9) (9 = Most Vigour (0-9) (9 = Deeper Greenness Dead) + (0-9) + Vigour) + (0-9) + Green) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days 14 Days 28 Days 1. Untreated 8.O 8.0 8.0 8.0 8.0 7.5 2. AN (Anthranilic Acid) 9.0 8.0 9.O 8.0 8.0 8.0 3. AC (Acetaminophen) 8.O 8.0 8.0 8.0 8.0 8.0 4. ANAC 8.O 8.0 8.0 8.0 8.0 8.0 5. AN + AC + Terpene 7.5 7.5 7.0 7.0 7.0 7.0 6. SAF 8.O 8.0 8.0 8.0 8.0 8.0 7. AN - SAF 7.5 8.0 7.5 8.0 7.0 7.5 8. AC - SAF 8.O 8.0 8.0 8.0 8.0 8.0 9. AN - AC - SAF 7.5 8.0 7.0 7.5 8.0 8.0 10. ANAC + SAF + 7.5 7.5 7.5 7.0 7.0 7.0 Terpene 11. 3.0 l/ha Isoproturon (500 6.5 3.5 7.0 6.0 8.0 8.0 g/I) (x1 rate) = IPU 12. 5.0 l/ha IPU (x2 rate) 7.0 3.0 7.0 5.5 7.5 8.0 13. 7.0 l/ha IPU (x3 rate) 7.0 2.5 6.5 S.O 7.0 8.0 14. x1 IPU - AN 6.O 4.0 6.5 6.5 8.0 7.5 15 x2 IPU - AN 7.0 3.0 7.0 6.0 8.0 7.5 16. x3 IPU - AN 7.0 3.0 7.0 6.0 8.0 7.5 17. x1 IPU - AC 7.0 3.0 7.0 S.O 7.5 8.0 18. x2 IPU - AC 7.0 3.0 6.0 S.O 7.5 8.0 19. x3 IPU - AC 6.5 3.0 7.0 S.O 8.0 8.0 20 x1 IPU - AN-AC 7.0 3.5 7.0 5.5 8.0 8.0 21 x2 IPU - AN-AC 7.0 3.5 7.0 5.5 8.0 8.0 22 x3 IPU - AN-AC 6.O 3.0 7.0 5.5 7.5 8.0 23. x1 IPU - SAF 6.O 4.5 6.5 6.5 7.5 8.0 24 x2 IPU - SAF 7.0 4.5 7.0 6.5 8.0 7.5 2S. x3 IPU - SAF 7.0 4.0 7.5 6.5 8.0 8.0 26. x1 IPU - AN - SAF 7.0 4.5 7.0 6.5 8.0 8.0 27. x2 IPU - AN - SAF 6.5 4.5 7.0 6.0 7.5 8.0 28. x3 IPU - AN - SAF 7.0 4.0 6.5 6.5 7.5 8.0 29. x1 IPU - AC - SAF 7.0 S.O 7.0 7.0 7.5 8.0 30. x2 IPU - AC - SAF 6.5 4.0 6.5 6.5 8.0 7.5 31. x3 IPU - AC - SAF 7.0 4.0 6.0 6.5 8.0 8.0 32. x1 IPU - AN - AC - SAF 7.0 S.O 6.0 7.0 8.0 8.0 33. x2 IPU - AN - AC - SAF 7.0 4.5 6.5 6.0 8.0 8.0 34. x3 IPU - AN - AC - SAF 6.5 4.0 7.0 6.0 8.0 7.5 35 x1 IPU - AN-AC- 7.0 5.5 7.0 7.0 8.0 7.0 SAF + Terpene 36. x2 IPU - AN-AC- 7.0 S.O 6.5 6.0 7.5 7.5 SAF + Terpene 37. x3 IPU - AN-AC- 7.0 S.O 6.0 6.0 8.0 7.5 SAF + Terpene 38. x1 IPU - AN-AC- 7.0 5.5 7.0 6.0 8.0 7.5 Terpene US 2012/0088.667 A1 Apr. 12, 2012 29

TABLE 3.4-continued

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENING SYSTEMAND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE ISOPROTURON

Phytotoxicity Vigour Greenness (0-9) (O = Phytotoxicity (0-9) (9 = Most Vigour (0-9) (9 = Deeper Greenness Dead) + (0-9) + Vigour) + (0-9) + Green) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days 14 Days 28 Days 39. x2 IPU + ANAC + 7.0 4.5 7.0 S.O 7.5 7.5 Terpene 40. x3 IPU + ANAC + 7.0 4.0 6.5 S.O 8.0 8.0 Terpene 41. PU + Terpene 7.0 4.5 7.0 S.O 8.0 7.5 42. x2 IPU + Terpene 7.0 4.0 6.5 S.O 7.5 8.0 43. PU + Terpene 7.0 3.5 7.0 S.O 7.0 8.0 x1 IPU fb (followed by) 7.0 3.5 7.0 S.O 8.0 8.0 AN + AC after 7 Days 45. PU f ANAC 7.0 3.5 7.0 4.5 8.0 8.0 after 7 Days 46. x3 IPU fib ANAC 7.0 3.0 6.5 4.5 8.0 8.0 after 7 Days 47. x1 IPU fib AN - AC - SAF 7.0 3.5 6.5 S.O 8.0 8.0 after 7 Days 48. x2 IPU fib AN - AC - SAF 6.O 3.5 7.0 4.0 7.5 7.5 after 7 Days 49. x3 IPU fib AN - AC - SAF 6.5 3.0 6.5 4.0 7.5 8.0 after 7 Days. SO. x1 IPU fib AN - AC - SAF 6.O 4.5 7.0 5.5 8.0 7.5 Terpene after 7 Days S1. x2 IPU fib AN - AC - SAF 6.5 4.5 7.0 4.0 8.0 7.5 Terpene after 7 Days 52. x3 IPU fib AN - AC - SAF 6.5 4.0 6.5 4.5 8.0 7.5 Terpene after 7 Days 53. PU f SAF after 7.0 4.0 7.0 S.O 8.0 8.0

54. X2 C b SAF after 6.5 3.0 7.0 4.0 8.0 8.0

55. b SAF after 7.0 4.0 7.0 4.5 8.0 8.0 7 Days

TABLE 3.5

WINTER WHEAT - CROP SAFENING BENEFITS FROMADDITION OF SAFENING SYSTEMAND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE FLUMIOXAZIN

Phytotoxicity Vigour Greenness (0-9) (O = Phytotoxicity (0-9) (9 = Most Vigour (0-9) (9 = Deeper Greenness Dead) + (0-9) + Vigour) + (0-9) + Green) + (0-9) + Treatment 14 Days 28 Days 14 days 28 Days 14 Days 28 Days Untreated 8.O 8.0 8.0 8.0 8.0 7.5 AN (Anthranilic Acid) 9.0 8.0 9.O 8.0 8.0 8.0 AC (Acetaminophen) 8.O 8.0 8.0 8.0 8.0 8.0 AN + AC 8.O 8.0 8.0 8.0 8.0 8.0 AN+AC + Terpene 7.5 7.5 7.0 7.0 7.0 7.0 SAF 8.O 8.0 8.0 8.0 8.0 8.0 AN-SAF 7.5 8.0 7.5 8.0 7.0 7.5 AC - SAF 8.O 8.0 8.0 8.0 8.0 8.0 AN + AC+ SAF 7.5 8.0 7.0 7.5 8.0 8.0 1 AN + AC+ SAF + 7.5 8.0 7.5 7.0 7.0 7.0 Terpene 1 1 . 75 mlha flumioxazin - 4.0 3.5 7.0 6.0 6.O 6.O Guillotine (300 g/I) - (x1 Rate) - Flux1 12. 100 mlha Flux2 4.0 3.0 7.0 6.0 6.O 6.O 13. 125 mlha Flux3 4.0 3.0 7.5 5.5 6.O 4.5 14. x1 Flu + AN 3.5 3.0 6.5 6.0 6.5 5.5 1S. x2 Flu + AN 3.5 3.0 6.5 6.0 6.5 6.O 16. x3 Flu + AN 4.0 3.0 7.0 5.5 6.O 4.5 17. x1 Flu + AC 4.5 3.5 7.5 6.0 6.O S.O 18. x2 Flu + AC 4.5 3.0 7.0 6.0 6.O S.O 19. x3 Flu + AC 4.0 3.0 6.5 5.5 6.O S.O 20. x1 Flu + AN + AC S.O 4.5 7.0 6.5 7.0 6.O

US 2012/0088.667 A1 Apr. 12, 2012 31

0158. As shown in Tables 3.1 to 3.5, each of the safening SAF: at least one from class (f) each at <3 g/1, plus at least one formulations showed a significant reduction in phytotoxicity from class (c). when applied to a range of species in combination with an Results are shown in Table 4. herbicide, when compared to the addition of herbicides alone. (0160 Thus the Safening systems improve crop Safening in a range 0.161 Statistical Analyses (Least Significant Difference, of species. An increase in vigour and greenness is also noted. 5% Level) for Table 4: Example 4 Safening of Glyphosate Herbicide (non-GM Maize, Phyto + Phyto + Phyto + Vigour + Vigour + Vigour + UK) 14 Days 28 Days 41 Days 14 Days 28 Days 41 Days 0159. Maize cv Sundance (i.e. not Roundup Ready) sown LSD 1.07 122 1.21 1.10 1.18 120 27 Apr. 2008, to obtain 1 even plant per 1 litre pot, grown in (5%) John Innes No 3 compost of pH 6.5. Treated with gly- Treat phospate, date of first spraying 15 June. Dates of measure- ment ment/scoring: 29 June, 13 July, 26 July. Means Statistical Layout: Randomised Complete Block trial, under glasshouse conditions, United Kingdom.

TABLE 4

MAIZE - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE GLYPHOSATE (360 g/l formulation). Phytotoxicity Phytotoxicity Phytotoxicity (0-9) (O = (0-9) (O = (0-9) (O = Vigour Vigour Vigour Dead) + Dead) + Dead) + (0-9) + (0-9) + (0-9) + Treatment 14 Days 28 Days 41 days 14 Days 28 Days 41 Days

1. Untreated 8.0 8.0 8.0 8.O 8.0 7.5 2. AN (Anthranilic Acid) 8.0 8.0 8.0 8.O 8.0 8.0 3. AC (Acetaminophen) 8.0 8.0 8.0 8.O 8.0 8.0 4. ANAC 8.0 8.0 8.0 8.O 8.0 8.0 5. AN + AC + Terpene 7.5 7.5 7.5 7.0 7.0 7.0 6. SAF 8.0 8.0 8.0 8.O 8.0 8.0 7. AN - SAF 7.5 7.5 8.0 8.O 7.0 7.5 8. AC - SAF 7.5 7.5 8.0 8.O 8.0 8.0 9. AN - AC - SAF 8.0 8.0 8.0 7.5 8.0 8.0 OAN + AC + SAF + 8.0 7.5 7.5 7.0 7.0 7.0 Terpene 10.5 l/ha Glyphosate 360 8.0 3.0 O.O 7.0 3.5 O.O (360 g/1) = G-360 below (= x1 rate) 21.0 l/ha G-360 (= “x2 8.0 3.0 O.O 7.0 3.0 O.O rate) 3 2.0 l/ha G-360 (= “x3' 8.0 3.0 O.O 7.0 3.0 O.O rate) 4 x1 G-360-AN 7.5 4.0 O.O 7.0 4.5 O.O 5 x2 G-360-AN 8.0 3.5 O.O 6.5 4.0 O.O 6 x3 G-360-AN 8.0 4.0 O.O 7.0 4.0 O.O 7 x1 G-360-AC 7.5 4.0 O.O 7.0 4.5 O.O 8 x2 G-360-AC 8.0 4.0 O.O 7.0 4.0 O.O 9 x3 G-360-AC 8.0 4.0 O.O 7.0 4.0 O.O 20 x1 G-360-AN - AC 8.0 6.0 4.0 7.0 5.5 4.0 21 x2 G-360 + AN+AC 8.0 6.0 3.5 7.0 S.O 4.0 22 x3 G-360-AN - AC 8.0 6.0 3.5 7.0 S.O 3.5 23 x1 G-360 - SAF 8.0 7.0 6.5 7.0 6.O 6.5 24 x2 G-360 - SAF 8.0 6.5 6.5 6.5 6.O 6.0 25 x3 G-360 - SAF 8.0 7.5 6.O 7.0 6.O 5.5 26 x1 G-360-AN-SAF 8.0 7.0 6.O 7.0 6.O 6.0 27 x2 G-360-AN-SAF 8.0 7.0 6.O 7.0 6.O 6.0 28 X3 G-360-AN - SAF 8.0 7.0 5.5 7.0 6.O 5.5 29 x1 G-360 - AC - SAF 8.0 6.5 6.O 7.0 6.O 6.0 30 x2 G-360-AC- 7.5 6.5 6.O 7.0 6.O 6.0 SAF 31 x3 G-360-AC- 7.5 6.0 6.5 7.0 6.O 6.0 SAF US 2012/0088.667 A1 Apr. 12, 2012 32

TABLE 4-continued

MAIZE - CROP SAFENING BENEFITS FROMADDITION OF SAFENER AND, OR ANTHRANILIC ACID AND, ORACETAMINOPEHEN TO THE HERBICIDE GLYPHOSATE (360 g/l formulation). Phytotoxicity Phytotoxicity Phytotoxicity (0-9) (O = (0-9) (O = (0-9) (O = Vigour Vigour Vigour Dead) + Dead) + Dead) + (0-9) + (0-9) + (0-9) + Treatment 14 Days 28 Days 41 days 14 Days 28 Days 41 Days

32x1 G-360 + AN+AC + 8.0 7.0 7.0 7.0 7.0 7.0 SAF 33 x2 G-360 + AN+AC + 8.0 7.0 7.0 7.0 7.0 6.5 SAF 34x3 G-360 + AN+AC + 8.0 7.0 6.O 7.0 7.0 6.5 SAF 35 x1 G-360 + AN+AC + 8.0 7.0 6.O 7.0 6.5 6.O SAF + Terpene 36 x2 G-360 + AN+AC + 8.0 7.0 6.O 7.0 6.5 6.O SAF + Terpene 37 x3 G-360-AN - AC- 8.0 7.0 6.O 7.0 6.5 6.O SAF + Terpene 38 x1 G-360 + AN+AC + 7.5 7.0 3.5 7.0 5.5 4.0 Terpene 39x2 G-360 + AN+AC + 7.5 6.5 3.5 7.0 5.5 3.5 Terpene 40x3 G-360 + ANAC + 7.5 6.5 4.0 7.0 5.5 3.5 Terpene 41 x1 G-360 + Terpene 8.0 6.5 O.O 7.0 S.O O.O 42 X2 G-360 + Terpene 8.0 6.O O.O 7.0 S.O O.O 43 x3 G-360 + Terpene 8.0 5.5 O.O 7.0 4.5 O.O 44x1 G-360 fb (followed by) 7.5 6.O O.O 7.0 5.5 O.O AN + AC after 7 Days. 45 x2 G-36Ofb ANAC 8.0 5.5 O.O 7.0 S.O O.O after 7 Days 46x3 G-36Ofb ANAC 8.0 S.O O.O 7.0 S.O O.O after 7 Days 47 x1 G-36Ofb AN-AC- 7.5 5.5 S.O 7.0 S.O 5.5 SAF after 7 Days 48 x2 G-36Ofb AN-AC- 8.0 S.O 5.5 7.0 S.O S.O SAF after 7 Days 49 x3 G-36Ofb AN-AC- 7.5 S.O 5.5 7.0 S.O 5.5 SAF after 7 Days. SOX1 G-360 fib AN-AC- 8.0 5.5 5.5 7.0 S.O S.O SAF + Terpene after 7 Days 51 x2 G-360 fib AN-AC- 8.0 6.O S.O 7.0 S.O S.O SAF + Terpene after 7 Days 52 x3 G-360 fib AN-AC- 8.0 5.5 5.5 7.0 S.O S.O SAF + Terpene after 7 Days S3 x1 G-360 ft SAF after 7 7.5 S.O 5.5 6.5 S.O 6.O Days 54x2 G-360 fb SAF after 7 7.0 S.O S.O 7.0 4.5 S.O Days SS x3 G-360 ft SAF after 7 7.0 S.O S.O 7.0 4.0 S.O Days

0162 Each of the Safening systems used to safen glypho- 0164. Two varieties Roundup ready soybean (glycine sate showed a reduction in phytotoxicity (measured on a scale of 0-9, where 0-dead and 9=least phytotoxicity). Vigour was max) Asgrow 3302 RR/STS and Pioneer 93M42 treated also boosted (measured on a scale of 0-9, where 0–least with glyphosate at crop growth stage V4-V5. Glyphosate was vigour and 9 most vigour). applied in the form of Roundup PowerMax, at a rate of 3.0 Example 5 l/ha. This is a high rate of glyphospate, which was used in Safening of Glyphosate Herbicide (GM Maize, Uni order to induce a phytotoxic response. versity of Illinois) 0163 Trial Details: Randomised complete block, with four replicates per treatment. Plot size=10 ftx30 ft 300 ft SAF: at least one from class (f) each at <3 g/1, plus at least one aca. from class (c). US 2012/0088.667 A1 Apr. 12, 2012 33

TABLE 5.1 Phytotoxicity and Yield Results Variety A - Asgrow 3302 RRSTS; Application timing: VA-VS trifoliate leaf stage. Mean 96 Yield Mean Phyto 21/7 Bushells Yield % Phyto - % Phyto - % Phyto- (four Per (4 Treatment Rate. Ha 21.7 3Of7 7/8 replicates) Acre reps) Roundup 3.00 + 18 3 O 18.0d 59.7 58.6 PowerMax -- SOO Liqui AMS - R1 Roundup 3.00 + 15 3 O 61.7 PowerMax -- SOO Liqui AMS - R2 Roundup 3.00 + 18 5 O 59.7 PowerMax -- SOO Liqui AMS - R3 Roundup 3.00 + 2O 5 O 53.4 PowerMax -- SOO Liqui AMS-R4 Roundup 3.00 + 8 O O S.Oe 62.6 60.9 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R1 Roundup 3.00 + 5 O O 60.8 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R2 Roundup 3.00 + 3 O O 52.5 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R3 Roundup 3.00 + 3 O O 67.7 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R4 Roundup 3.00 + 8 O O 6.Oe 6O.O 58.3 PowerMax + 5.00 + Liqui 1.00 AMS AN+AC + SAF R1 Roundup 3.00 + 5 O O 50.4 PowerMax + 5.00 + Liqui 1.00 AMS AN+AC + SAF R2 Roundup 3.00 + 5 O O 51.6 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF R3 Roundup 3.00 + 7 O O 71.O PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF R4 US 2012/0088.667 A1 Apr. 12, 2012 34

TABLE 5.1-continued

Phytotoxicity and Yield Results Variety A - Asgrow 3302 RRSTS; Application timing: V4-V5 trifoliate leaf stage.

Mean 96 Yield Mean Phyto 21/7 Bushells Yield % Phyto - % Phyto - % Phyto- (four Per (4 Treatment Rate. Ha 21.7 3Of7 7/8 replicates) Acre reps)

Roundup 3.00 + 5 O O S.Oe 58.4 61.8 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R1 Roundup 3.00 + 7 O O 59.3 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R2 Roundup 3.00 + 3 O O 60.8 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R3 Roundup 3.00 + 5 O O 68.6 PowerMax + 5.00 + Liqui 1.00 AMS SAF-R4 Roundup 3.00 + 5 O O 6.Oe 61.O SS.1 PowerMax + 5.00 + Liqui 1.00 AMS AN+AC + SAF POL - R1 Roundup 3.00 + 5 O O 55.7 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL - R2 Roundup 3.00 + 5 O O 53.8 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL - R3 Roundup 3.00 + 7 3 O 49.8 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL - R4 LSD (5%) 1.65 1.35 O.81 7.00 Means St Dew O.83 O.68 O41 3.54 US 2012/0088.667 A1 Apr. 12, 2012 35

TABLE 3.2 Phytotoxicity and Yield Results Variety B - Pioneer 93M42. Application timing: V4-V5 trifoliate leaf stage.

Mean 96 Phyto Yield Mean % (four Bushells Yield % Phyto - Phyto - % Phyto - replicates) - Per (4 Treatment Rate. Ha 21.7 307 7/8 21.7 Acre reps)

Roundup 3.00 + 22 3 O 24.0c 54.2 55.5 PowerMax -- SOO Liqui AMS - R1 Roundup 3.00 + 22 5 O SS.6 PowerMax -- SOO Liqui AMS - R2 Roundup 3.00 + 25 8 O 52.9 PowerMax -- SOO Liqui AMS - R3 Roundup 3.00 + 28 5 O 59.4 PowerMax -- SOO Liqui AMS-R4 Roundup 3.00 + 12 3 O 11.0d 57.7 57.4 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R1 Roundup 3.00 + 15 O O 56.4 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R2 Roundup 3.00 + 8 3 O 59.O PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R3 Roundup 3.00 + 8 O O 56.4 PowerMax + 5.00 + Liqui 1.00 AMS AN + AC R4 Roundup 3.00 + 15 3 O 12.0d 52.2 55.2 PowerMax + 5.00 + Liqui 1.00 AMS AN+AC + SAF R1 Roundup 3.00 + 10 O O 55.8 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF R2 Roundup 3.00 + 10 O O S3.6 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF R3 US 2012/0088.667 A1 Apr. 12, 2012 36

TABLE 3.2-continued Phytotoxicity and Yield Results Variety B - Pioneer 93M42. Application timing: V4-V5 trifoliate leaf stage.

Mean 96 Phyto Yield Mean % (four Bushells Yield % Phyto - Phyto - % Phyto - replicates) - Per (4 Treatment Rate. Ha 21.7 307 7/8 21.7 Acre reps)

Roundup 3.00 + 12 3 O 59.3 PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF R4 Roundup 3.00 + 12 3 O 12.0d 55.2 57.5 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R1 Roundup 3.00 + 15 O O 61.5 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R2 Roundup 3.00 + 10 O O 56.5 PowerMax + 5.00 + Liqui 1.00 AMS SAF - R3 Roundup 3.00 + 10 3 O 56.6 PowerMax + 5.00 + Liqui 1.00 AMS SAF-R4 Roundup 3.00 + 7 O O 9.0d 54.2 57.3 PowerMax + 5.00 + Liqui 1.00 AMS AN+AC + SAF POL - R1 Roundup 3.00 + 10 O O 56.O PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL - R2 Roundup 3.00 + 8 O O 6O.O PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL - R3 Roundup 3.00 + 12 5 O 59.O PowerMax + 5.00 + Liquid 1.00 AMS AN+AC + SAF POL-R4 LSD (5%) 2.42 1.94 O.92 3.66 St Dew 122 1.OO O46 1.85 US 2012/0088.667 A1 Apr. 12, 2012 37

0.165. Each of the safening systems showed a statistically 0171 (d) a purine or pyrimidine nucleoside, nucleotide significant reduction in % phytotoxicity (Duncan's Multiple or a metabolic precursor thereof, egadenine, adenosine, Range Test at 95% probability level: letters which are differ thymine, thymidine, cytosine, guanine, guanosine, ent between mean values are statistically different). This hypoxanthine, uracil, uridine or inosine, to act as struc reduction in % phytotoxicity was seen for each of the two varieties of soybean. Yields were improved as a consequence. tural precursors for nucleic acid synthesis. No notable difference between the effectiveness of any of the 0172 (e) a naturally occurring fat or oil including olive, safening systems was evident. Soya, coconut and corn (Oil) oils; 0173 (f) an amino acid of a type that occurs naturally in Example 6 plant proteins, eg glycine (GLY), alanine (AL), valine, Safening Oilseed Rape Using a Variety of Safening leucine (LE), isoleucine, serine, threonine (THR), cys Systems teine (CY), methionine (ME), aspartic acid, glutamic 0166 Safening systems were applied to crops of oilseed acid, glutamine (GLU), asparagine (AS), lysine (LY), rape and winter wheat treated with various herbicides hydroxylysine, arginine, histidine, phenylalanine, (Bilfenox (with insecticide), Carbetamide, Propaquizafop), tyrosine, tryptophan, proline, or hydroxyproline. either without or withoutAN and/or AC. The safener/safening Statistical Layout: Randomised Complete Block trial, under system and the herbicide were applied to the crops either glasshouse conditions, United Kingdom. simultaneously or sequentially. 0167 Safening compounds were selected from the list of 0.174 Statistical Analyses (Least Significant Difference, compounds below. The compounds used are highlighted in 5% Level) for Table 6.1: bold. 0168 (a) Glucose (GL), hydrolysed starch, sucrose (S), Table 6.1: fructose (FR), glycerol (G), glyceraldehydes, erythrose, ribulose, Xylulose or arabinose or an ester or glycoside 0175 or metabolic equivalent of Such a carbohydrate; 0169 (b) an organic acid of the Krebs Tricarboxylic Acid Cycle or a metabolic precursor thereof (including Phyto + Phyto + Vigour + 14 Vigour + 28 Rooting + 28 citric (C). Succinic (SU), malic, pyruvic, acetic and 14 Days 28 Days Days Days Days fumaric acids); 0170 (c) a vitamin or coenzyme, eg thiamine (T), ribo LSD (5%) 1.01 1.12 1.07 1.14 1.15 flavin (R), pyridoxine (P), pyridoxamine, pyridoxal, Treatment nicotinamide (N), folic acid (F), ascorbic acid (AA), Means Biotin (B) and vitamin B12(B12) or a precursor thereof including nicotinic acid

TABLE 6.1

OILSEED RAPE - CROP SAFENING BENEFITS FROMADDITION OF WARIOUS SAFENING COMPOUNDS FROM CATEGORIES (a) to (f) ABOVE, TO THE HERBICIDE BIFENOX (with insecticide). EXAMPLES ARE SHOWN WITH AND WITHOUTANTHRANILIC ACID, ANTHRANILIC ACID - ACETAMINOPEHEN Phytotoxicity Phytotoxicity Vigour Vigour Rooting (0-9) (O = (0-9) (O = (0-9) (O = (0-9) (O = (0-9) (9 = Best Dead) + Dead) + Dead) + Dead) + Rooting) + Treatment 14 Days 28 Days 14 days 28 Days 28 Days 1. Untreated 7.5 7.5 7.5 8.0 8.O 2. AN (Anthranilic Acid) 8.0 8.O 8.O 8.0 8.O 3. AC (Acetaminophen) 8.0 8.O 8.O 8.0 8.O 4. AN + AC 8.0 8.O 8.O 8.0 8.O 5. 1.0 l/ha Bifenox (480 g/l) + 6.O S.O 6.O 5.5 6.O cypermethrin (rec rate) = X1 Bif+ C 6.1.5 ha Bilfenox + x1 5.5 5.5 6.O 5.5 S.O cypermethrin = x2 Bif+ C 7.2.0 ha Bilfenox + x1 S.O 4.5 S.O 4.5 4.5 Cypermethrin = x3 Bif + C 8. x3 Bif+ C+AN 9. x3 Bif + C + AN + AC 5.5 5.5 5.5 S.O 5.5 With added Category (a) Safeners (10-33)

10x1 Bif+ C+ GL 7.0 7.0 7.0 6.5 8.O 11 x2 Bif + C + GL 7.0 6.5 8.O 7.0 7.0 12 x3 Bif+ C+ GL 6.5 6.O 7.0 6.5 7.0 12 x3 Bif + C + AN + GL 6.5 6.O 7.0 6.5 7.0

US 2012/0088.667 A1 Apr. 12, 2012 45

TABLE 6.1-continued

OILSEEDRAPE - CROP SAFENING BENEFITS FROMADDITION OF WARIOUS SAFENING COMPOUNDS FROM CATEGORIES (a) to (f) ABOVE, TO THE HERBICIDE BIFENOX (with insecticide). EXAMPLES ARE SHOWN WITH AND WITHOUTANTHRANILIC ACIDANTHRANILIC ACID - ACETAMINOPEHEN Phytotoxicity Phytotoxicity Vigour Vigour Rooting (0-9) (O = (0-9) (O = (0-9) (O = (0-9) (O = (0-9) (9 = Best Dead) + Dead) + Dead) + Dead) + Rooting) + Treatment 14 Days 28 Days 14 days 28 Days 28 Days 263 x3 Bif + C + AN + AC + 6.O 5.5 6.0 5.5 7.0 AA+ B12 With added Category (a) + (c) + (e) + (f) Safeners (264-268)

264x1 Bif + C + Oil + ME + 7.0 6.5 6.0 6.5 7.0 G + R+N 265 x2 Bif+ C + Oil + ME + 6.5 6.5 6.0 6.O 7.0 G + R+N 266x3 Bif+ C + Oil + ME + 6.5 7.0 6.5 6.O 7.5 G + R+N 267 x3 Bif + C ++AN + Oil + 6.5 7.0 6.5 6.O 7.0 ME- G - R - N 268 x3 Bif + C + AN + AC + 6.5 7.0 7.0 6.5 7.5 ME- G - R - N

TABLE 6.2

OILSEED RAPE - CROP SAFENING BENEFITS FROMADDITION OF VARIOUS SAFENING COMPOUNDS FROM CATEGORIES (a) to (f) ABOVE, TO THE HERBICIDE CARBETAMIDE (60% w/w) + PROPAQUIZAFOP (100 g/I). EXAMPLES ARE SHOWN WITH AND WITHOUTANTHRANILIC ACID, ANTHRANILIC ACID - ACETAMINOPEHEN. Phytotoxicity Vigour Vigour Rooting (0-9) (O = Phytotoxicity (0-9) (O = (0-9) (O = (0-9) (9 = Dead) + (0-9) (O = Dead) + Dead) + Best 14 Dead) + 14 28 Rooting) + Treatmen Days 28 Days days Days 28 Days 1. Untreated 7.5 7.5 7.5 8.0 8.O 2. AN 8.0 8.O 8.O 8.0 8.O 3. AC 8.0 8.O 8.O 8.0 8.O 4. AN + AC 8.0 8.O 8.O 8.0 8.O 5. 2.5 kg/ha 6.O S.O 6.O S.O 6.O Carbetamide + 0.5 ha Propaquizafop = x1 Car + Prop 6.3.5 kg/ha 5.5 4.5 S.O Carbetamide + 0.7 ha Propaquizafop = x2 Car + Prop 7. 4.5 kg/ha 5.5 4.0 4.0 4.5 Carbetamide + 0.8 ha. Propaquizafop = x3 Car + Prop 8. X3 Car + Prop + 5.5 4.0 4.0 4.5 AN 9. X3 Car + Prop + 5.5 4.0 4.5 S.O AN + AC With added Category (a) Safeners (10-33) 10x1 Car + Prop + 6.5 6.5 7.5 7.0 7.5 GL 11 x2 Car + Prop + 7.0 7.0 6.5 7.0 7.0 GL 12 x3 Car + Prop + 6.5 6.5 6.5 6.O 7.0 GL

US 2012/0088.667 A1 Apr. 12, 2012 57

TABLE 6.2-continued

OILSEED RAPE - CROP SAFENING BENEFITS FROMADDITION OF VARIOUS SAFENING COMPOUNDS FROM CATEGORIES (a) to (f) ABOVE, TO THE HERBICIDE CARBETAMIDE (60% w/w) + PROPAQUIZAFOP (100 g/I). EXAMPLES ARE SHOWN WITH AND WITHOUTANTHRANILIC ACID, ANTHRANILIC ACID - ACETAMINOPEHEN. Phytotoxicity Vigour Vigour Rooting (0-9) (O = Phytotoxicity (0-9) (O = (0-9) (O = (0-9) (9 = Dead) + (0-9) (O = Dead) + Dead) + Best 14 Dead) + 14 28 Rooting) + Treatment Days 28 Days days Days 28 Days

251 x3 Car - 6.5 6.5 6.5 6.O 7.0 Prop + Oil + F + T - R. 252 x3 Car - 7.0 6.5 6.5 6.5 7.0 Prop + AN + Oil +

253 x3 Car - 7.0 6.5 7.0 7.0 7.0 Prop + ANAC + Oil + F + T + R 254 x1 Car + 7.0 7.0 7.0 6.5 6.5 Prop + Oil +

255 x2 Car - 6.5 6.5 6.5 6.O 6.5 Prop + Oil + AA+ B - B12 256 x3 Car - 6.5 6.5 6.O 6.O 7.0 Prop + Oil + AA+ B - B12 257 x3 Car - 6.5 6.5 6.5 6.5 7.0 Prop + AN + Oil +

258 x3 Car - 7.0 7.0 7.0 7.0 7.5 Prop + ANAC +

259 x1 Car - 7.0 6.5 7.0 7.0 7.0 Prop + Oil + AA+ B12 260 x2 Car + 7.0 6.5 7.0 6.5 7.0 Prop + Oil + AA+ B12 261 x3 Car + 7.0 7.0 6.O 6.O 6.5 Prop + Oil + AA+ B12 262 x3 Car + 7.0 7.0 6.5 6.5 6.5 Prop + AN + Oil +

263 x3 Car + 7.0 7.0 7.0 7.0 7.5 Prop + ANAC +

With added Category (a) + (c) + (e) + (f) Safeners (264-268)

264x1 Car + 6.5 7.0 6.5 6.5 7.0 Prop + Oil + ME +

265 x2 Car - 6.5 6.5 6.O 6.O 6.5 Prop + Oil + ME- G - R - N 266x3 Car + 6.5 6.5 6.5 6.O 6.5 Prop + Oil + ME +

267 x3 Car - 6.5 6.5 6.O 6.5 7.0 Prop + AN + Oil + ME- G - R - N 268 x3 Car + 6.5 7.0 6.5 6.5 7.0 Prop + AN+AC + ME- G - R - N US 2012/0088.667 A1 Apr. 12, 2012

0176 A reduction in phytotoxicity, along with increases in Co=100% Cobalt Sulphate (20g per litre and per hectare). vigour and rooting, are shown from the use of the Safening FF1=20 g per litre Cobalt Sulphate (as per Co above) plus systems above (either combinations of compounds from “Miracle-Gro’ at x1 recommended rate (applied at 15 g per classes (a) to (f) alone or in combination AN and/or AC) in 2.5 sq metres). Miracle-Gro contains: 24% N, 4% P, 13% K. combination with a herbicide, in contrast to application of a plus 0.02% B, 0.03% Cu, 0.19% Fe, 0.05% Mn, 0.001% Mo herbicide alone. and 0.03% Zn. FF2=20 g per litre Cobalt Sulphate plus Miracle-Gro at x2 recommended rate. Example 7 SAF: at least one from class (f) each at <3 g/1, plus at least one from class (c). Root Nodulation and Safening in a Range of Nitro gen-Fixing Crops Example 7.1 Soybean 0177 Safening systems were applied to crops of soybean, 0.178 Scored/Counted+28 Days After Spraying. Sown in navy bean and pea either alone or in combination with cobalt Compost of low pH (5.0-5.5) on 1 May 2008. Spray Date and/or a general foliar fertilizer, either without or without AN (VC)=4 June, V1 Date=20 June. Scored/Measured on 17 July. and/or AC. The safener/safening system and the fertiliser Each treatment is the mean result of 12 plants, within four were applied to the crops either simultaneously or sequen replicates. Seed density approx 110 kg/ha. Soybean treated tially. with standard inoculant at Sowing.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) Untreated 24.O 4.9 29.0 5.4 7.6 6.0 AN 28.2 5.3 33.2 5.8 8.0 6.2 AC 26.1 5.0 28.1 5.3 8.0 6.O AN + AC 31.2 5.5 33.3 5.8 8.3 6.5 AN-SAF 33.0 5.8 34.O 5.9 8.6 6.2 AC - SAF 31.4 5.5 29.3 5.4 8.6 6.1 AN + AC+ 37.2 6.O 41.2 6.5 8.6 7.1 SAF 8 AN + AC+ 33.0 5.8 34.3 5.9 8.6 6.8 SAF - POL Co 27.3 5.2 28.8 5.4 7.8 6.0 Co + AN 3O.O 5.5 31.5 5.7 8.0 6.0 Co - AC 26.9 5.2 28.9 5.4 8.0 6.0 Co + AN+ 32.1 5.7 35.9 6.O 8.4 6.5 AC Co + AN+ 33.3 5.8 37.7 6.3 8.7 6.2 SAF Co - AC + 28.1 5.3 33.3 5.8 8.7 6.1 SAF Co + AN+ 37.1 6.1 41.6 6.5 8.7 6.8 AC - SAF Co + AN+ 36.4 6.O 38.4 6.3 8.6 6.8 AC+ SAF + POL 26.2 S.O 28.8 5.4 8.0 6.0 8 FF1 - AN 27.8 5.3 33.2 5.8 8.3 6.3 FF1 - AN-- 32.4 5.7 36.1 6.O 8.7 6.3 SAF FF1 - AN-- 32.7 5.7 36.3 6.O 8.4 6.8 AC 21 FF1 - AN-- 35.9 6.O 410 6.5 8.7 7.0 AC - SAF 22 FF1 - AN-- 36.2 6.O 38.0 6.3 8.6 6.9 AC+ SAF + POL 23 FF2 26.7 S.1 28.2 5.3 8.0 6.0 24 FF2 - AN 29.2 5.4 31.0 S.6 8.3 6.3 25 FF2 - AN-- 31.7 S.6 34.O 5.9 8.7 6.4 SAF 26 FF2 - AN-- 33.1 5.8 33.8 5.9 8.5 6.5 AC 27 FF2 - AN-- 36.4 6.1 40.8 6.5 8.7 6.8 AC - SAF US 2012/0088.667 A1 Apr. 12, 2012

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 28 FF2 - AN-- 35.1 6.0 40.1 6.4 8.7 6.8 AC+ SAF + POL LSD 3.21 O.SO 3.38 0.53 O.48 O.S2 (Treatment Mean) 5%

Example 7.2 Glycine max (Soybean) 0179 Dates as per Example 7.1 above, but sown in com post of normal pH (6.5). Each treatment represents the mean values for 12 plants, within four replicates. Sowing density 110 kg/ha. Standard inoculant applied at Sowing.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) Treatment (V1) (V1) (VC) (VC) (V1) (V1) 1 Untreated 26.9 5.2 29.1 S.4 7.4 6.5 2 AN 34.2 5.9 33.3 5.8 8.0 6.7 3 AC 29.9 5.5 32.O 5.7 8.0 6.5 4 AN + AC 36.0 6.O 37.8 6.2 8.3 7.1 5 AN-SAF 34.0 5.9 37.6 6.2 8.6 6.5 6 AC - SAF 33.9 5.9 31.9 5.7 8.6 6.5 7 AN + AC+ 37.0 6.2 38.1 6.3 8.7 7.8 SAF 8 AN + AC+ 35.7 6.O 35.7 6.O 8.5 7.6 SAF - POL 9 Co 29.8 5.5 28.0 5.3 8.0 6.5 O Co + AN 3O.O 5.5 32.5 5.7 8.0 6.4 1 Co - AC 30.2 5.5 28.2 5.3 8.0 6.5 2 Co + AN+ 33.3 5.8 35.6 6.O 8.0 7.0 AC 3 Co + AN+ 35.8 6.O 33.0 5.8 8.7 6.7 SAF 4 Co - AC + 32.2 5.7 28.1 5.3 8.7 6.5 SAF 5 Co + AN+ 37.0 6.2 37.8 6.2 8.7 7.6 AC - SAF 6 Co + AN+ 35.7 6.O 35.3 6.O 8.7 7.4 AC+ SAF + POL 7 29.8 5.5 32.8 5.7 8.0 6.5 8 FF1 - AN 29.7 5.5 34.0 5.9 8.0 6.7 9 FF1 - AN-- 33.1 5.8 36.1 6.1 8.7 6.7 SAF 2O FF1 - AN-- 33.2 5.8 39.1 6.4 8.0 7.1 AC 21 FF1 - AN-- 35.5 6.O 42.1 6.7 8.7 7.8 AC - SAF 22 FF1 - AN-- 35.7 6.O 40.1 6.5 8.6 7.6 AC+ SAF + POL 23 29.5 5.5 32.3 5.7 8.0 6.5 24 FF2 - AN 30.2 S.6 33.9 5.9 8.0 6.8 25 FF2 - AN-- 33.6 5.8 37.3 6.2 8.7 6.9 SAF 26 FF2 - AN-- 33.7 5.8 39.3 6.4 8.2 7.1 AC 27 FF2 - AN-- 36.0 6.O 42.6 6.7 8.7 8.0 AC - SAF US 2012/0088.667 A1 Apr. 12, 2012 60

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) Treatment (V1) (V1) (VC) (VC) (V1) (V1) 28 FF2 - AN-- 35.8 6.0 40.1 6.5 8.7 7.6 AC+ SAF + POL LSD 3.42 O.S3 3.58 (Treatment Mean) 5%

Example 7.3 Phaseolus vulgaris (Navy Bean) 0180 NAVY BEAN cv Mogex. Scored/Counted+28 Days after Spraying. Sown in Compost of low pH (5.0-5.5) on 29 Apr. 2008. Spray Date (VC)=27 May, V1 Date=16 June. Scored/Measured on 11 July. Each treatment represents the mean value of 12 plants, within four replicates. No inoculum applied.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) Untreated 18.2 3.0 21.1 3.4 5.5 5.8 AN 20.9 3.3 23.4 3.8 6.O 6.O AC 19.3 3.1 22.1 3.5 S.6 6.O AN + AC 22.2 3.5 25.2 4.0 6.1 6.5 AN-SAF 22.1 3.5 24.1 3.9 6.5 6.O AC - SAF 20.8 3.3 23.9 3.9 6.5 6.O AN + AC+ 31.1 4.9 27.1 4.3 7.2 6.9 SAF 8 AN + AC+ 29.3 4.6 26.7 4.2 6.6 6.6 SAF - POL Co 21.0 3.3 23.8 3.8 5.7 5.9 Co + AN 22.3 3.5 25.2 4.0 6.2 6.O Co - AC 20.8 3.3 23.6 3.7 5.7 5.9 Co + AN+ 25.1 4.0 26.0 4.1 5.9 6.5 AC Co + AN+ 25.3 4.0 26.9 4.2 6.5 6.8 SAF Co - AC + 23.6 3.7 25.3 4.0 6.6 6.8 SAF Co + AN+ 26.9 4.3 28.3 4.5 6.7 7.1 AC - SAF Co + AN+ 26.5 4.2 26.9 4.3 6.5 6.8 AC+ SAF + POL FF 21.9 3.5 23.5 3.7 5.8 6.2 8 FF1 - AN 23.8 3.7 25.2 4.0 5.7 6.3 FF1 - AN-- 23.7 3.8 2S.O 4.0 6.4 6.8 SA FF1 - AN-- 23.8 3.8 26.1 4.1 6.O 6.4 AC 21 FF1 - AN-- 27.0 4.3 28.3 4.5 6.8 6.8 AC - SAF 22 FF1 - AN-- 26.2 4.1 30.3 4.8 6.8 6.7 AC+ SAF + POL 23 FF2 23.2 3.6 23.6 3.7 5.8 6.1 24 FF2 - AN 24.0 3.8 24.7 3.9 5.7 6.2 25 FF2 - AN-- 23.9 3.8 26.1 4.1 6.7 6.6 SA US 2012/0088.667 A1 Apr. 12, 2012 61

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 26 FF2 - AN-- 24.2 3.9 25.3 4.0 6.O 6.4 AC 27 FF2 - AN-- 26.9 4.1 28.4 4.5 6.8 6.8 AC - SAF 28 FF2 - AN-- 25.3 4.0 26.8 4.3 6.8 6.8 AC+ SAF + POL LSD 2.15 O.32 2.23 O.34 O.47 0.55 (Treatment Mean) 5%

Example 7.4 Phaseolus vulgaris (Navy Bean) 0181 NAVY BEAN cv Mogex. Scored/Counted+28 Days after Spraying. Dates as per Example 7.3. Above, but sown in compost of normal pH (6.5). Each treatment represents the mean value from 12 plants, within four replicates. No inocu lum applied.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) Untreated 29.7 4.8 31.1 4.9 7.0 6.8 AN 32.2 S.O 33.2 S.1 7.0 7.2 AC 29.5 4.8 32.1 S.O 7.0 7.0 AN + AC 34.1 5.2 34.8 5.3 7.5 7.0 AN-SAF 32.O S.O 36.2 5.5 7.2 7.0 AC - SAF 33.2 S.1 3S.O 5.4 7.2 7.0 AN + AC+ 38.1 5.8 38.0 5.8 7.8 7.8 SAF 8 AN + AC+ 36.0 5.5 38.1 5.8 7.6 7.2 SAF - POL Co 33.5 5.2 31.8 S.O 7.3 7.2 Co + AN 36.2 5.5 34.2 5.3 7.5 7.0 Co - AC 33.7 5.2 31.6 S.O 7.5 7.0 Co + AN+ 35.9 5.5 34.4 5.3 7.5 7.5 AC Co + AN+ 36.3 5.5 38.0 5.8 7.5 7.0 SAF Co - AC + 34.2 5.3 36.0 5.5 7.5 7.2 SAF Co + AN+ 37.3 S.6 37.9 5.8 8.0 7.9 AC - SAF Co + AN+ 3S.O 5.4 37.5 5.7 7.5 7.5 AC+ SAF + POL FF1 32.O S.O 33.8 5.2 7.8 7.5 8 FF1 - AN 34.9 5.3 34.7 5.3 7.8 7.4 FF1 - AN-- 35.1 5.4 35.1 5.4 7.8 7.5 SAF FF1 - AN-- 34.6 5.3 35.2 5.4 7.8 7.5 AC 21 FF1 - AN-- 38.1 5.8 38.2 5.8 7.8 7.5 AC - SAF 22 FF1 - AN-- 37.9 5.8 38.0 5.8 7.8 7.8 AC+ SAF + POL 23 FF2 32.8 S.1 31.8 S.O 7.8 7.2 24 FF2 - AN 34.6 5.3 33.8 5.2 7.3 7.5 US 2012/0088.667 A1 Apr. 12, 2012

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 25 FF2 - AN-- 3S.O 5.4 36.1 5.5 7.3 7.5 SAF 26 FF2 - AN-- 37.3 S.6 36.0 5.5 7.8 7.5 AC 27 FF2 - AN-- 37.9 5.8 38.3 5.8 7.2 7.5 AC - SAF 28 FF2 - AN-- 38.1 5.8 37.7 5.7 7.5 7.8 AC+ SAF + POL LSD 3.08 0.37 3.14 O.39 O46 O.S3 (Treatment Mean) 5%

Example 7.5 Pisum sativum (Pea) 0182 PEA TRIAL 5-cv Ragtime. Scored/Counted+ 28 Days after Spraying. Sown in Compost of Low pH (5.0- 5.5) on 28 Apr. 2008. Spray Date (VC)=26 May, V1 Date=14 June. Scored/Measured on 9 July. Each treatment represents the results from 12 plants, within four replicates. No inocu lum applied.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 1 Untreated S.1 4.8 17.4 5.2 5.2 S.O 2 AN 6.8 S.O 17.3 5.2 5.2 5.5 3 AC 6.7 S.O 17.3 5.2 5.2 S.1 4 AN + AC 9.9 5.5 19.8 5.5 5.4 6.O 5 AN-SAF 7.0 S.1 19.9 5.5 6.7 5.8 6 AC - SAF 6.6 S.O 18.8 5.4 6.5 5.8 7 AN + AC+ 22.2 5.8 22.2 5.8 7.5 6.5 SAF 8 AN + AC+ 22.4 5.8 21.9 5.7 7.2 6.2 SAF - POL 9 Co 6.4 S.O 18.1 5.3 S.1 5.8 O Co + AN 7.2 5.2 19.7 5.5 5.5 5.5 1 Co - AC 7.4 5.2 17.9 5.3 5.3 5.5 2 Co + AN+ 9.7 5.5 19.7 5.5 5.5 5.8 AC 3 Co + AN+ 9.8 S.6 22.2 5.8 6.5 6.5 SAF 4 Co - AC + 7.2 5.2 21.3 5.7 6.4 6.O SAF 5 Co + AN+ 9.6 5.5 22.1 5.8 6.5 6.5 AC - SAF 6 Co + AN+ 9.4 5.5 22.3 5.8 6.5 6.2 AC+ SAF + POL 7 FF1 6.7 S.O 17.3 5.2 6.O 6.5 8 FF1 - AN 6.5 S.O 18.1 5.3 6.O 6.5 9 FF1 - AN-- 6.4 S.O 19.1 5.4 6.5 6.7 SAF 2O FF1 - AN-- 6.6 S.O 19.5 5.5 6.1 6.8 AC 21 FF1 - AN-- 6.7 S.O 22.1 5.8 6.5 7.0 AC - SAF 22 FF1 - AN-- 6.7 S.O 22.2 5.8 6.5 7.2 AC+ SAF + POL US 2012/0088.667 A1 Apr. 12, 2012

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 23 FF2 16.5 S.O 16.4 S.O 6.O 6.2 24 FF2 - AN 17.3 5.2 17.0 5.2 6.O 6.1 25 FF2 - AN-- 18.1 5.3 17.2 5.2 6.2 6.7 SAF 26 FF2 - AN-- 2O.O 5.5 17.2 5.2 6.1 6.3 AC 27 FF2 - AN-- 21.7 5.7 22.3 5.8 6.2 7.0 AC - SAF 28 FF2 - AN-- 20.6 S.6 21.1 5.7 6.2 7.0 AC+ SAF + POL LSD 1.71 O.33 1.85 0.36 O.48 OSO (Treatment Mean) 5%

Example 7.6 Pisum sativum (Pea) 0183 PEA TRIAL 7.6-cv Ragtime. Dates as per Example 7.5 above, but sown in compost of normal pH (6.5). Each treatment represents the results from 12 plants, within four replicates. No inoculum was applied.

Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 1 Untreated 15.1 4.8 15.3 4.8 7.0 6.8 2 AN 17.2 5.2 17.1 5.2 7.0 6.9 3 AC 15.4 4.9 16.4 S.O 7.0 6.7 4 AN + AC 17.3 5.2 16.4 S.O 7.1 6.6 5 AN-SAF 17.2 5.2 16.5 S.O 7.6 7.0 6 AC - SAF 16.8 S.1 16.3 S.O 7.5 6.9 7 AN + AC+ 23.6 6.O 23.8 6.O 8.0 7.5 SAF 8 AN + AC+ 22.0 5.8 22.7 5.9 7.8 7.2 SAF - POL 9 Co 16.9 S.1 17.4 5.2 6.9 6.8 O Co + AN 17.6 5.2 17.5 5.2 7.0 6.8 1 Co - AC 16.7 S.1 17.3 5.2 7.0 6.8 2 Co + AN+ 19.6 5.5 19.6 5.5 7.0 6.8 AC 3 Co + AN+ 19.7 5.5 19.5 5.5 7.4 6.8 SAF 4 Co - AC + 19.7 5.5 17.4 5.2 7.6 6.8 SAF 5 Co + AN+ 19.6 5.5 22.1 5.8 7.9 7.6 AC - SAF 6 Co + AN+ 19.2 5.4 17.9 5.3 7.8 7.1 AC+ SAF + POL 7 FF1 23.7 6.O 2S.O 6.2 6.9 6.8 8 FF1 - AN 23.9 6.O 23.6 6.O 6.9 6.9 9 FF1 - AN-- 23.6 6.O 23.5 6.O 7.3 6.7 SAF 2O FF1 - AN-- 22.1 5.8 23.5 6.O 7.4 6.7 AC 21 FF1 - AN-- 22.0 5.8 23.6 6.O 7.8 7.6 AC - SAF 22 FF1 - AN-- 23.0 5.9 23.5 5.9 7.9 7.3 AC+ SAF + POL US 2012/0088.667 A1 Apr. 12, 2012

-continued Phyto Nodules Nodules Nod Toxicity Vigour Per Nodulation Per Score Score Score Plant Score (0-9) Plant (0-9) (0-9) (0-9) No. Treatment (V1) (V1) (VC) (VC) (V1) (V1) 23 FF2 23.7 6.0 23.6 6.O 7.1 6.8 24 FF2 - AN 22.2 5.8 22.3 S.8 6.9 6.8 25 FF2 - AN - 22.4 5.8 23.2 S.9 7.3 6.8 SAF 26 FF2 - AN - 22.4 5.8 21.1 S.7 7.0 6.8 AC 27 FF2 - AN - 22.2 5.8 210 5.7 7.9 7.0 AC - SAF 28 FF2 - AN - 22.4 5.8 22.3 S.8 7.6 6.8 AC+ SAF + POL LSD 1.73 O.32 1.75 0.35 0.49 O.S2 (Treatment Mean) 5%

Example 7.7 V1 (first true leaf stage). Such improvements would be highly advantageous from application as seed treatments, either Pisum sativum (Pea) applied alone or in combination with other seed treatments available e.g. fungicides, insecticides or those intended for 0184 PEA Comparison of Nodulation Results with any other purpose. Rooting Results: i.e. whereas under low pH conditions, nodu lation was significantly improved by addition of various treat Example 8 ments, rooting was not improved under these conditions (data from Example 7.5). Sowing details etc as per Example 7.5. Safening of Herbicides from Addition of Auxin? AuXin Precursor and Acetaminophen 0187 Cultural Details: winter wheat cv Alchemy, sown 15 Phyto- Apr. 2009, at seven seeds per 9 cm pot, sown in normal pH Nodules Rooting Toxicity multi-purpose compost. Date of spraying: 14 May. Dates of Per Nodulation Score Score measurement/scoring: 28 May, 11 June. No. Treatment y so 2. 2. 0188 The following auxins or precursors were compared, each at 10 Molar solutions. Addition of acetaminophen 1 Untreated 15.1 4.8 4.2 5.2 (AC) was at 3 g per hectare equivalent in each case. Phyto 32 ANAC 16.816.7 S.O 4.2 5.2 toxicity reduction is on a 0-9 scale, where 0-dead plant. 4 AN + AC 19.9 5.5 4.2 5.4 5 AN-SAF 17.0 S.1 4.1 6.7 6 AC - SAF 16.6 S.O 4.2 6.5 7 AN + AC+ 22.2 5.8 4.2 7.5 Phytotoxicity Phytotoxicity SAF (0-9: (0-9: 8 AN + AC+ 22.4 5.8 4.2 7.2 O = dead) + O = dead) + SAF - POL Treatment 14 Days 28 Days 9 Co 16.4 S.O 4.2 S.1 10 Co + AN 17.2 5.2 4.2 5.5 Untreated 8.0 8.0 11 Co - AC 17.4 5.2 4.1 5.3 Acetaminophen (AC) 8.0 8.0 12 Co + AN+ 19.7 5.5 4.2 5.5 Anthranilic acid (AN) 8.0 8.0 AC Anthranilic acid + AC 8.0 8.0 13 Co + AN+ 19.8 S.6 4.2 6.5 75 mlha flumioxazin - Guillotine 4.0 3.5 SAF (300 g/l) (x1 rate) - Flux1 14 Co - AC + 17.2 5.2 4.2 6.4 100 mlha Flux2 4.0 3.0 SAF 125 mlha Flux3 3.5 3.0 15 Co + AN+ 19.6 5.5 4.2 6.5 x1 Flu + AC 4.0 3.5 AC - SAF x2 Flu + AC 3.5 3.0 16 Co + AN+ 19.4 5.5 4.2 6.5 x3 Flu + AC 3.5 3.0 AC+ SAF + x1 Flu + AN 4.0 3.0 POL x2 Flu + AN 3.5 3.0 LSD 1.71 O.33 O.48 O.49 x3 Flu + AN 3.5 3.0 (Treatment x1 Flu + AN + AC S.O 4.5 Mean) 5% x2 Flu + AN + AC S.O 4.0 x3 Flu + AN + AC S.O 4.0 x3 Flu + Anthranilic acid methyl ester 3.5 3.0 0185. The addition of safeners or a safening system (AME) greatly reduced any phytotoxicity x3 Flu + AME + AC S.O 4.5 x3 Flu + Acetamide 3.0 3.0 0186 The improvements in the degree of nodulation were x3 Flu + Acetamide + AC 4.5 4.5 obtained by applications at either VC (cotyledon stage) or at US 2012/0088.667 A1 Apr. 12, 2012 65

(IAA), 4-chloro-indole-3-acetic acid (4-Cl-IAA), phenylace -continued tic acid (PAA), indole-3-butyric acid (IBA), indole-3-acetyl 1-O-B-D-glucose (IAAglc); or a synthetic auxin selected Phytotoxicity Phytotoxicity (0-9: (0-9: from 1-naphthaleneacetic acid (NAA), 2,4-dichlorophenoxy O = dead) + O = dead) + acetic acid (2,4-D), 2-methoxy-3,6-dichlorobenzoic acid (di Treatment 14 Days 28 Days camba), 4-amino-3,5,6-trichloropicolinic acid (tordon), 2.4. x3 Flu + Anthranilic 3.5 3.5 5-trichlorophenoxyacetic acid (2,4,5-T), 2,3,6- Acid monosodium salt trichlorobenzoic acid or N,N-dimethylethylthiocarbamate. x3 Flu + Anthranilic 4.0 4.5 Acid monosodium salt + AC 34. The composition according to claim 33 wherein the x3 Flu + Indole-3-acetamide 3.5 3.0 conjugate of the natural auxin is IAA-Inositol, IAA-Inositol x3 Flu + Indole-3-acetamide + AC S.O 4.5 arabinose, IAP1, an IAA-peptide, an IAA glycoprotein, an x3 Flu + 3-Hydroxyanthranilic acid 3.5 3.5 x3 Flu + 3-Hydroxyanthranilic acid + 4.5 4.5 IAA-glucan, IAA-aspartate, IAA-glucose, IAA-1-O-glu AC cose, IAA-myo-Inositol. IAA-4-O-glucose, IAA-6-O-glu x3 Flu + Tryptamine 3.0 3.5 cose, IAA-Inositol-galactose, an IAA amide conjugate, oran x3 Tryptamine + AC 4.0 4.5 IAA-amino acid conjugate. 35. The composition according to claim 26 wherein the 0189 Addition of an auxin/auxin precursor plus acetami metabolite is indole-3-lactic acid or indole-3-ethanol. nophen provides a benefit to safening improvement (phyto toxicity reduction). 36. The composition according to claim 26 wherein the 0.190 All publications mentioned in the above specifica composition further comprises cobalt. tion are herein incorporated by reference. Various modifica 37. The composition according to claim 26 wherein the tions and variations of the described methods and systems of composition further comprises a compound selected from: the invention will be apparent to those skilled in the art with a) glucose, hydrolysed starch, Sucrose, fructose, glycerol, out departing from the scope and spirit of the invention. glyceraldehydes, erythrose, ribulose, Xylulose or arabi Although the invention has been described in connection with nose, monosaccharides including aldoses such as D-Ri specific preferred embodiments, it should be understood that bose, D-Xylose, L-Arabinose, D-Glucose, D-Mannose the invention as claimed should not be unduly limited to such and D-Galactose; ketoses such as D-Ribulose and specific embodiments. Indeed, various modifications of the D-Fructose; deoxyaldoses such as 2-Deoxy-D-ribose, described modes of carrying out the invention which are L-Fuccose; acetylated amino Sugars such as N-Acteyl obvious to those skilled in the field are intended to be within D-glucosamine and N-Acetyl-D-galactosamine; acidic the scope of the following claims. monosaccharides such as D-Glucuronic acid, L-Idu 1.-25. (canceled) ronic acid and N-Acetylneuraminic acid, Sugar alcohols 26. A composition comprising an auxin, an auxin precur such as D-Sorbitol and D-Mannitol, disaccharides Sor, an auxin metabolite or a derivative of said auxin, auxin including maltose, lactose and Sucrose, or an ester or precursor or auxin metabolite and acetaminophen or a deriva glycoside or metabolic equivalent of Such a carbohy tive thereof for use as a plant safener. 27. The composition according to claim 26 wherein the drate; auxin is an indolic auxin or a phenolic auxin. b) an organic acid of the Krebs tricarboxylic acid cycle or 28. The composition according to claim 26 wherein the a metabolic precursor thereof; auxin derivative is an acid, a conjugate, a salt, an ester, or an c) a vitamin or coenzyme, or a precursor thereof; amide of the auxin, or an alkylated or halogenated auxin. d) a purine or pyrimidine nucleoside, nucleotide or meta 29. The composition according to claim 28 wherein the bolic precursor thereof; auxin is conjugated to a Sugar, an alcohol, an amino acid or a protein. e) a naturally occurring fat or oil; or 30. The composition according to claim 26 wherein the f) an amino acid. precursor is chorismate, anthranilic acid, phosphoribosyl 38. The composition of claim 37 wherein the compound is anthraniliate, 1-(O-carboxyphenulamino)-1-deoxyribulose selected from c) a vitamin or coenzyme, or a precursor 5-phosphate, indole-3-glycerol-phosphate, indole, indole-3- thereof; d) a purine or pyrimidine nucleoside, nucleotide or acetic acid, trytophan, tryptamine, N-hydroxy tryptamine, metabolic precursor thereof, or f) an amino acid. indole-3-acetaldoxime, 1-aci-nitro-2-indolylethane, indolic 39. The composition of claim 26 wherein the composition glucosinate, indole-3-acetonitrile (IAN), indole-3-acetalde further comprises at least one of a fungicide, an insecticide, a hyde, indole-3-lactic acid, indole-3-pyruvic acid, or indole herbicide, a chemical thinning agent, a fertiliser, a plant 3-ethanol. growth regulator and an abscission delay agent. 31. The composition according to claim 30 wherein the precursor is anthranilic acid or a derivative thereof; wherein 40. A method of protecting a desired plant from the effect the anthranilic acid derivative is preferably a conjugate, a salt, of an agrochemical comprising applying an effective amount an ester, or an amide of anthranilic acid, optionally Substi of the composition of claim 26. tuted with an alkyl or halogen group. 41. The method of claim 40 wherein the composition is 32. The composition according to claim 31 wherein the applied by at least one of seed treatment, localised soil treat anthranilic acid derivative is conjugated to a Sugar, an alcohol, ment, plant treatment, including seedling treatment. an amino acid, a peptide or a protein. 42. The method of claim 40 wherein the application of the 33. The composition according to claim 26 wherein the composition is in advance of the application of the agro auxin is a natural auxin selected from indole-3-acetic acid chemical. US 2012/0088.667 A1 Apr. 12, 2012 66

43. A method for improving plant safety comprising the 45. The method of claim 40 wherein the composition is application of the composition of claim 26 to a plant or its applied at conditions of at least one of low or high pH, tem environs. perature, Salinity or drought. 44. The method of claim 40 wherein application of the composition further provides a boost in plant vigour. ck