Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

• the present invention relates to a method for the prevention/treatment of bark beetle and/or wood borer infestation of trees comprising treatment of the tree with a composition comprising a macroyclic lactone.
• the present invention relates to the use of emamectin benzoate in a method for the prevention/treatment of bark beetle infestation of trees.
• the southern pine beetle Dendroctonus frontalis Zimmerman
• mountain pine beetle D. ponderosae Hopkins
• the western pine beetle D. brevicomis LeConte
• the spruce beetle D. rufipennis Kirby
• the Douglas fir beetle D. pseudotsugae Hopkins
• the pine engraver Ips pini Say
• the pi ⁇ yon ips I. confuses LeConte
• California five-spined ips I.
• the beetles bore into the trees and mated adults dig galleries and channels under the bark. Eggs deposited in these channels hatch into larvae which feed on the cambium layer beneath the bark. The channels they form cut off the supply of water and nutrients and result in the death of the tree.
• the beetles may also carry fungi on their bodies which can germinate and spread within the trees—such fungi may also change the colour of the wood.
• SPB southern pine beetle
• D. frontalis Zimmermann D. frontalis Zimmermann
• dicrotophos Although tree mortality was not prevented by any of the treatments, dicrotophos was found to significantly reduce both egg gallery length and subsequent brood production. Because dicrotophos has a relatively high mammalian toxicity, it is not available to the general public. Oxdydementon methyl (Metasystox-R) applied by Mauget injectors (Inject-a-cide®) is registered for use against several Dendroctonus and Ips species of bark beetles, but is not registered for SPB.
• Emamectin benzoate an avermectin derivative, has shown systemic activity in pine and is highly effective against pine wood nematode, Bursaphelenchus xylophilis (Steiner & Buhrer) Nickle (Takai et al. 2000, 2001, 2003a, 2003b), and coneworm, Dioryctria spp. (Grosman et al. 2002), with protection lasting more than three years.
• Denim® emamectin benzoate
• the present invention provides a method for the prevention/treatment of bark beetle and/or wood borer infestation of trees comprising treatment of the tree with a composition comprising a macroyclic lactone.
• a macrocyclic lactone compound is a compound having a ring in its chemical structure made up of twelve or more atoms.
• the atoms may be selected from carbon, oxygen, nitrogen or sulphur, preferably the atoms are carbon and oxygen.
• the ring has up to 20 atoms.
• Examples include spinosad (737), avermectin and avermectin monosaccharide derivatives, such as abamectin (1), doramectin (25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)avermectin A 1a ; CAS RN 117704-25-3), emamectin (291), eprinomectin ((4′′R)-4′′-(acetylamino)-4′′-deoxyavermectin B 1 ; CAS RN 123997-26-2), ivermectin (5-O-demethyl avermectin A 1a (i) mixture with 5-O-demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)avermectin A 1a (ii), CAS RN 70288-86-7 (70161-11-4+70209-81-3)) and selamectin (
• the natural Avermectins which can be obtained from Streptomyces avermitilis, are referred to as A1a, A1b, A2a, A2b, B1a, B1b, B2a and B2b.
• the compounds referred to as “A” and “B” have a methoxy radical and an OH group, respectively, in the 5-position.
• the “a” series and the “b” series are compounds in which the substituent R 1 (in position 25) is a sec-butyl radical and an isopropyl radical, respectively.
• the number 1 in the name of the compounds means that carbon atoms 22 and 23 are linked by double bonds; the number 2 means that they are linked by a single bond and that the C atom 23 carries an OH group.
• the pesticides including spinosad, abamectin, milbemectin and emamectin, are described in the e-Pesticide Manual, version 3.0, 13th Edition, Ed. CDC Tomlin, British Crop Protection Council, 2003-04. The number following the compound name is the entry number given in the Pesticide Manual.
• the macrocylic lactone is a compound of formula (I):
• R1 to R9 represent, independently of each other hydrogen or a substituent
• n 0, 1 or 2;
• n 0, 1, 2 or 3;
• bonds marked with A, B, C, D, E and F indicate, independently of each other, that two adjacent carbon atoms are connected by a double bond, a single bond, a single bond and an epoxide bridge of the formula
• E/Z isomer including, where applicable, an E/Z isomer, a mixture of E/Z isomers, and/or a tautomer thereof, in each case in free form or in salt form.
• the compound of formula (I) may be in the form of tautomers. Accordingly, hereinbefore and hereinafter, where appropriate, the compound (I) is to be understood to include corresponding tautomers, even if the latter are not specifically mentioned in each case.
• the compounds above are capable of forming acid addition salts.
• Those salts are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulphuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C1-C4 alkane carboxylic acids, for example acetic acid, saturated or unsaturated dicarboxylic acids, for example oxalic, malonic, succinic, maleic, fumaric or phthalic acid, hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulphonic acids, such as unsubstituted or substituted, for example halo-substituted, C1-C4 alkane- or aryl-sulphonic acids,
• salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metals salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethyl-, diethyl-, triethyl-, or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, for example, mono-, di- or tri-ethanolamine.
• corresponding internal salts may also be formed.
• any reference hereinbefore or hereinafter to the free compounds of formula (I) or to its salt is to be understood as including also the corresponding salts or the free compounds of formula (I) where appropriate and expedient.
• the invention is concerned with a compound of the formula (II):
• R1 is methyl or ethyl
• This compound is known as 4′′-deoxy-4′′-N-methylamino avermectin B1a/B1b or emamectin. It is noted that when R1 is a ethyl group, the compound is the B1a form and when R1 is methyl, the compound is the B1b form.
• the compounds are used as a mixture of the two forms, B1a and B1b, since the structural differences are very slight and amount to the difference between sec-butyl group and an isopropyl group, and the two compounds have substantially the same chemical reactivity and biological activities.
• the nomenclature B1a/B1b is employed to indicate the individual compounds and the mixture of such compounds.
• compositions contain 80% or more of the B1a component and 20% or less of the B1b component, more preferably 90% or more of the B1a component and 10% or less of the B1b component.
• the present invention is concerned with the acid addition salt of the above compound.
• the acid may be benzoic acid, benzoic acid substituted with one, two or three substitutents selected from the group consisting of halogen, hydroxyl, carboxyl, C1-C6 alkyl and C1-C6 alkoxyl, benzene sulphonic acid, citric acid, phosphoric acid, tartaric acid or maleic acid.
• the preferred acid addition salts are formed with benzoic acid, salicyclic acid, gallic acid, benzenesulphonic acid an citric acid.
• the most preferred acid addition salt is that formed with benzoic acid and the compound comprising this salt is known as emamectin benzoate.
• the active ingredient of the present invention may be applied to trees in any of the ways known in the art, e.g. spraying.
• the preferred method of application is via tree injection techniques and, in particular, via the Arborjet Tree IVTM microinfusion system (Arborjet, Inc. Woburn, Mass.).
• the active ingredient may be formulated ways any one of a number of known ways and, in particular, may be formulated for use in tree injection methods.
• the active ingredient may be dissolved in a solvent to which a surfactant may be added and it can be applied together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.
• Suitable solvents are: aromatic hydrocarbons, e.g. xylene mixtures or substituted naphthalenes, phthalates, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulphoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
• aromatic hydrocarbons e.g. xylene mixtures or substituted naphthalenes
• phthalates such as dibutyl phthalate or dioctyl phthalate
• aliphatic hydrocarbons
• suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
• surfactants will also be understood as comprising mixtures of surfactants.
• the intent of the study was to evaluate the efficacy of systemic injections of emamectin benzoate in reducing success of pine bark beetle attacks on loblolly pine and determine the duration of treatment efficacy.
• SPB populations were extremely low in Texas in 2004, Ips engravers beetles were used as indicator species.
• Two 20-year-old, recently thinned loblolly pine plantations were selected on land owned by Temple-Inland Forest Products Corporation about 5 km south of Wells (Angelina County), Tex. Trees in one plantation were injected for use in a bolt study (Example 1). Trees in a 0.2 ha section of the second plantation were injected as part of a single-tree protection study (Example 2). A staging area also was set up in the second plantation where bolts from the first plantation were exposed to bark beetles and wood borers.
• packets of bark beetle pheromones (racemic ipsdienol+lanerione combination, ipsenol or cis-verbenol; Phero Tech, Inc., Delta, BC, Canada) were attached separately to three 1 m stakes evenly spaced in the study area. Racemic ipsdienol and cis-verbenol were used with the second and third series of bolts deployed in July and September, respectively. The packets were removed after 2 weeks when signs of attacks (boring dust) were observed on most test bolts, signaling that naturally-produced pheromones were present.
• a clear panel of acetate (10 cm wide by 25 cm long) was attached to the center of each bolt after deployment of bolts to monitor arrival of bark beetles.
• the top surface of each panel was coated entirely with Stikem Special® trapping compound (Michel and Pelton, Emeryville, Calif.). The traps were left in place for two weeks.
• each series of bolts were retrieved about 3 weeks after deployment, after observing many cerambycid egg niches on the bark surface of most bolts. There was concern that if cerambycid larvae were allowed to develop too long, their feeding activity would obscure or obliterate the Ips galleries. Thus, each series of bolts were retrieved and stored temporarily in a TFS seedling cooler ( ⁇ 45° F.) to slow cerambycid development until the bolts could be evaluated.
• Treatment efficacy was determined by comparing Ips beetle attacks and egg gallery length and cerambycid feeding on treated and untreated bolts.
• the data were transformed by log 10 (x+1) to satisfy criteria for normality and homoscedasticity (Zar 1984) and analyzed by GLM and the Fishers Protected LSD test using the Statview statistical program.
• Loblolly pine 15-20 cm DBH, were selected in the second plantation in March 2004.
• Each treatment (the same as those used in Example 1) was injected into four cardinal points about 0.3 m above the ground on each of 6 trees in April (16-23) using the Arborjet Tree IVTM system. After 5 weeks post-injection (May 28), frills were cut with a hatchet into the sapwood between the injection points near the base of the tree.
• a cellulose sponge was inserted into each cut and loaded with 10 ml of a 4:1 mix of sodium N-methyldithiocarbamate (MS) (Woodfume®; Osmose, Inc., Buffalo, N.Y.) plus dimethyl sulfoxide (DMSO) (Aldrich Chemical) (Roton 1987, Strom et al. 2004).
• MS sodium N-methyldithiocarbamate
• DMSO dimethyl sulfoxide
• a clear panel of acetate (10 cm wide by 25 cm long) coated with Stickem Special® was attached 2 m high on standing trees after deployment of pheromone baits to monitor arrival of bark beetles. The traps were left in place for two weeks.
• each tree was evaluated by marking a 30 cm section of bole at a height of 3 m. All visible Ips attacks and cerambycid egg niches were counted within the marked area. The number of trees with fading crowns also was recorded. Thereafter, the trees were evaluated weekly for crown fading. When mortality did occur, the trees were felled and two bolts taken and evaluated for attack success and gallery length as described in Example 1. All remaining trees were felled 66 days (March 9) after initial pheromone deployment when no additional trees had died for 3 weeks. Treatment efficacy was determined by comparing tree survival, beetle attacks and egg gallery length on treated and untreated bolts. As before, data were transformed and analyzed by GLM and the Fisher's Protected LSD test using the Statview statistical program.
• emamectin benzoate was highly effective in preventing successful attacks by Ips bark beetles and cerambycids one, three and five months after injection. On the bolts, at least, those male Ips that initiated attacks were either deterred or killed upon penetration into the phloem layer and exposure to the active ingredient. It is surmised that any pheromone production by males as they burrow through the bark was halted prematurely. Without these pheromones, very few, if any, females were attracted to the host material or entered the nuptial chamber to mate and begin construction of egg galleries.
• the emamectin benzoate dose (0.2 g ai/inch of tree diameter) used in 2004 has been found to prevent successful attack by Ips engravers. If a lower dose were to be injected in trees at the leading edge of an active SPB infestations, the injected trees may serve as trap trees, i.e. allow successful mass attack, gallery construction and egg laying by adult SPB, but the larvae would not develop and no brood adults would be produced. If the treatment proved successful, it is conceivable that local populations of SPB would decline and the progression of the infestation would stop.
• Emamectin 3.0 ab 100.0 0.0 a 0.0 3.0 a

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• Life Sciences & Earth Sciences (AREA)
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• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
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• Chemical And Physical Treatments For Wood And The Like (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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