OA10290A

OA10290A - Improved compositions for nematode control

Info

Publication number: OA10290A
Application number: OA60826A
Authority: OA
Inventors: Jeanette Tracy Ahlgrim; James Web Kassebaum; Barry James Shortt; James Michael Warner
Original assignee: Monsanto Co
Priority date: 1993-11-09
Filing date: 1996-05-07
Publication date: 1997-10-07
Also published as: JPH09506085A; NO961863L; WO1995012977A1; SK50896A3; ZA948828B; CN1134656A; HUT75106A; FI961949A0; HU9601243D0; BR9408011A; CZ129196A3; FI961949A7; AU8078594A; NO961863D0; BG100581A; CA2173160A1; FI961949L; EP0723397A1

Abstract

The present invention provides novel compositions, unexpectedly advantageous for controlling nematode, insect or acarid infestation of a plant, comprising a quantitatively variable combination of a compound of formula (I) in combination with selected adjuvants from among the typical wetting, dispersing or emulsifying agents, preferably, for example Tergitol3.

Description

IMPROVED COMPOSITIONS FOR NEMATODE CONTROL

Field of the invention

The présent invention relates to unexpectedly improved novelcompositions that contain a compound active on foliage in downward 5 systemic control of plant pests, ie parasitic nematodes, insects and acaridinfestation. The composition is a compound, particularly as disclosed inU.S. application Serial Number 07/827,231, filed February 3, 1992, winch isa continuation-in-part of U.S. Serial number 07/663,218, filed March 1,1991, incorporated herein by reference therefor, and published in the 10 Patent Coopération Treaty application Number PCT/US92/1474, incombination with an adjuvant selected from among typical wetting,dispersing or emulsifying agents used in agricultural formulations. Theinvention relates also to a method for controlling nematodes, insects, andacarids and to the use of the novel compositions. 15 Background of the Invention

It is well-known to use wetting, dispersing or emulsifying agents in fluorinated alkene-containing nematocidal, insecticidal, or acaricidalcompositions. For example, the above noted U.S. application discloses useof a blend of the calcium sait of dodecylbenzene sulfonate and nonionic 6- 20 molar ethylene oxide condensation product of nonylphenol, a blend of thecalcium sait of dodecylbenzene sulfonate and a nonionic 30-molar ethyleneoxide condensation product of nonyl phénol, a nonionic paste ofpolyalkylene giycol ether, refined xylene solvent and preferably Tween 20.

See also the above noted application, U.S. Patent 4,950,666, and 25 U.S. 4,876,285 for other typical surface-active wetting dispersing, and emulsifying agents used in agricultural formulations. For example, suchagents indude the alkyl and alkylaryl sulfonates and sulfates and theirsodium salts; alkylamide sulfonates, including fatty methyltaurides;alkylaryl polyether aîcohols, sulfated higher alcohols, polyvinyl alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonatedpetrolewn oils; fatty acid esters of polyhydric alcohols and the ethyleneoxide addition products of such esters; and the addition products of long*chain mercaptans and ethylene oxide. 5 Additionally, U.S. Patent Nos. 5,237,100, 5,236,938, and 5,232,949 disclose nematocides in compositions together with adjuvants includingsynergists exemplified as piperonyl butoxide or sesamex.

However, there remains a need in the art for nematocide,insecticide, or acaridicide compositions having improved plant uptake, 10 systemic mobility, and desirably low effective levels of use.

Summarv of the Invention

The présent invention provides compositions for controllingnematode, insect or acarid infestation of a plant, comprising aquantitaüvely variable combination of a compound of the formula I having 15 the structure

X

\.Ç-(CH2)n- QY Z 20 wherein:: n = 1, 3, 5, 7, 9, or 11; Q is CK2NHRe, CH2NO2, CH2N=CHR2, CH2N=C=O, CH2N+R3R4R5W-, 25 or (C=O)-Rn; X, Y, and 2 are independently H or F, provided that at least cne of X and Y is F, and further provided that when Q is(C=O)-R]j each of X, Y, and Z is F; W' is an agronomically acceptable anion; 30 R2 is an ærcmatic group; 3 v 1 <) 2 9 each of Rg, R4, and R5 is independently hydrogen; a lower alkyl group, optionally substituted with at least one groupselected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio,carboxyl, alkoxy-carbonyl, and phenyl; one of R3, R4, and R5 ishydroxy and the other two are hydrogen; or R3, R4, and R5 takentogether with the nitrogen of Q form a cyclic quatemaryammonium group;

Rg is hydrogen; an aliphatic group, optionally substituted with at least one group selected from hydroxy, alkoxy,halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, andphenyl; an amino acid amide of Q; (C=O)-R7; C1-C12 aliphaticamines, optionally substituted with at least one group selectedfrom hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio,carboxyl, alkoxycarbonyl, and phenyl; C2-C12 aliphatic carboxylic acids, their esters, thiol esters, and amides, ail optionallysubstituted with at least one group selected from hydroxy, alkoxy,halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, andphenyl; dihydro-3-oxo-pyrazolidinyl; or phenyl or thiophene,optionally substituted with at least one group selected fromhydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl,alkoxycarbonyl, and phenyl; or Rg taken with the nitrogen of Q is guanidine; hydrazine; alkyl or aryl hydrazine, optionally substituted with atLeast one group selected from hydroxy, alkoxy, halo, nitro, amino,ahiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; or an alkylor aryl sulfonamide, optionally substituted with at least onegroup selected from hydroxy, alkoxy, halo, nitro, amino, thiol,alkylthio, carboxyl, alkoxycarbonyl, and phenyl; R7 is (C=O>-Ri4; C1-C12 aliphatic group optionally substituted with at least one group selected from hydroxy, a]koxy,halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, andphenyl; C2-C12 aliphatic carboxylic acid, esters, thiol esters, oramides thereof, ail optionally substituted with at least one group 5 selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; or a N, O, or S group suchthat when taken with the carboxamide is a urea, semicarbazide,carbamate, or thiocarbamate group, ail optionally substitutedwith an alkyl or aryl group, optionally substituted with at least 10 one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxy-carbonyl, and phenyl;

Rjl is -OR^2> _SRi2> halogen, -NHOH, or -NR12R13 whereineach of R12 an^ R13 is independently hydrogen; analiphatic or an aromatic group, optionally substituted with at 15 least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; a C1-C12 aliphatic amine, optionally substituted with at least one groupselected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio,carboxyl, alkoxycarbonyl, and phenyl; a C2-C12 aliphatic 20 carboxylic acid, esters, amides and salts thereof, optionally substituted with at least one group selected from hydroxy, alkoxy,halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, andphenyl; or Rj2 ar-^ ^13 taken together with the N of Rji are a 25 protein amino acid or a cyclic group selected from morpholine, piperidine, piperazine, or pyrrolidine, optionally substituted withat least one group selected from hydroxy, alkoxy, halo, nitro,amino. thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;

Rj4 is OE. alkcxv, ΝΉ2· 0Γ NHNH2; 30 or any agronomicallv acceptable sait thereof; 5 v i ί together with or in combination with an activity enhancing amount of anadjuvant of the (a) formula II which is alkyl glycosides wherein the alkyl groupis a mixture of from about eight to fourteen carbons and the number of 5 glycoside groups présent in the formula are from one to about six butpreferably one to two, and more preferably APG 325 or APG 225 where thealkyl group is a mixture of from nine to eleven carbons or Atplus 258 oreither Hhodonat LMO which is coconut oil based sucroglyceride orRhodouat MLP 704 which is modified LMO sucroglyceride; 10 (b) formula III which is a quatemized fatty amine ethoxylate wherein the fatty amine is an alkylamine wherein the alkyl group is amixture of from about eight to twenty carbon atoms, preferably a mixtureof from eight to sixteen carbon atoms, more preferably a mixture of fromeight te twelve carbon atoms such as is found in cocomethyl ammonium 15 chioride, and most preferably Ethoquad C/12 (the quaternized fatty amineethoxylate may be represented by the formula

(EO)xH

R20R2X-(EO)yH Z 20 wh ereiu; R20 a mixture of alkyl groups of from about eight to twenty-twocarbon atoms, inclusive; î<2l *s an alkyl of from one to four carbons, inclusive; 25 EO is an ethylene oxide monomer wherein x and y are indepenêently a number of from zéro to fourteen and are the number ofmoles of ethoxvlation présent with the proviso that x and y taken togethermust be from two to fourteen, preferably two; and Z- is an agronomically acceptable anion); 6 k (c) formula IV which is a mixture of a fatty amine ethoxylateand ethoxylated alkylphenol, preferably Improve® (the fatty amineethoxylaue may be represented by the formula

R22N

(EO)nH

(EO)mH wherein: 10 B22 represents a mixture of alkyls of from about six to thirty carbons, inclusive, preferably from about twelve to twenty carbons,inclusive, EO is an ethyleneoxide monomer; and n and m represent the number of moles of ethoxylation in the15 formula and are when taken together about from one to fifty, preferably five to fifteen, and the ethoxylated alkylphenol may be represented by theformula 20

R

-O(EO)wH wherein: R23 is a mixture of alkyl groups of from zéro to twenty carbons, inclusive, preferably from about eight to ten carbons, inclusive, and morepreferably nine carbons; 25 EO is an ethylene oxide monomer; and w is the number of moles of ethoxylation in the formula and is from aboui two ro twenty, inclusive, and preferably from six to ten moles,inclusive); (d formula V which are ethoxylated acetylated diols, preferably30 Surfynol 4S5, and more preferably présent in the range from about 0.5% (the ethoxylated acetylated diols may be represented by the formula 7 v i G 2 9 0

wherein: 10 * is a number of carbons to provide a total number of carbons in the chain of from 10 through 12 carbons, inclusive; and EO is an ethyleneoxide monomer wherein q and p independently are numbers whichrep resent the number of moles of ethylene oxide monomers in the formulaanc are when taken together in the range of from about 10 through 30, 15 inclusive, preferably 30); (e) formula VI which is a secondary alcohol ethoxylate whereinthe number of moles of ethylene oxide monomers is from 7 to 15, inclusive,preferably Tergitol® 15-S-7, Tergitol® 15-S-9, or Tergitol® 15-S-12, andmore preferably Tergitol® 15-S 12 (the formula VI may be shown as 20 follews:

25 wherein: r>24a represents hydroxy or a Polyoxyethylene group wherein a represents the number of moles of ethylene oxide monomers présent in the formula and is from about seven to fifteen, inclusive, preferably about 30 nine to twelve, inclusive, and C* represents the ends of the carbon chain such that altogether the chain is a mixture of carbons having a total of

from eleven to fifteen carbons, inclusive, preferably from twelve tofourteen carbons, inclusive); (f) formula VII which is an alkoxylated fatty amine oxide,preferably Emcol XE 1656, including ethoxylated fatty amine oxide,preferably Flo-Mo 3153 (the alkoxylated fatty amine oxide is represented bythe formula 0' R'

R 25 N+-(CHCH2Ok—H

(CHCH2O^-H wherein Ü25 represents a mixture of alkyls of from about six to thirty carbons, Inclusive, preferably from about twelve to twenty carbons,inclusives ff is hydrogen or methyl; and n and zj represent the number of moles of alkoxylation or preferably ethoxvlation in the formula and are when taken together aboutfrom one to fifty, preferably five to fifteen); ..g) formula VIII which is an alkyldimethyl amine oxide, preferably Empigen OB (the alkyldimethyl amine oxide may berepresenned by the formula ο' R26-N+-CH3 ch3 whereên R20 represents a mixture of alkyls of from about six to thirty carbons, inclusive, preferably from about twelve to twenty carbons,inclusive; (h) formula IX which is a fatty alcohol polyglycol ether,preferably Genapol T250 or Neodol (the fatty alcohol polyglycol ethermay be represented by the formula î

R22-O(CHCH2^2-OH w ne rem R27 represents a mixture of alkyls of from about six to thirtycarbons. inclusive, preferably from about twelve to twenty carbons,inclusive; R' represents alkyl of from about one to two carbons,inclusive; Z-2 represents the number of moles of ethoxylation in theformula and are when taken together about from one to fifty, preferablyfive to furie en (i; formula X which is a fatty acid esterified polyethoxyether,preferably Kaomul 230 or which is stearic acid polyethoxylate,preferably Simusol M52( the coco esterfied polyethoxyether and stearicacre polyethoxylate may be represented by the formula 10 t b 290 R-28 CO2 (EO^- wherein R28 represents a mixture of alkyls of from about six to thirty carbcns, inclusive, preferably from about twelve to twenty carbons,inclusive; EO represents ethoxylation in the formula and Z3 is from oneto fifty, preferably five to fîfteen);or (j) formula XI which is a quatemary ammonium, preferablyDodigen 226 (the quatemary ammonium may be represented by theformula r29 —n+(Ch3)2(Ch2(c6h5)) q’ wherein R 2s represents alkyl from C8 to C20, preferably CIO to C16 and Q is an agronomically acceptable anion); (k) formula XII which is a quatemary ammonium,preferably Dodigen 4022 (the quatemary ammonium may berepres-ented by the formula R30R31R32N+(EO)n](PO)n2 Q' wherein R30. R31 and R32 are independently alkyls of from one to threecarbons which together are from two to seven carbons, preferably ailmethyL, or one of R30, R31. R32 is ((EO)ni(PO)n2); EO is ethylene oxide; P O is propylene oxide; nj is an integer of one to two; and n2 is an iuteger of three to fîfteen, preferably six to ten; and Q is an azToncmically acceptable anion); (l) formula XIII which is diamine ethoxylate, preferablyEthoduomeen (the diamine ethoxylate may be represented by theformula

(EO)n3 (ÉO)n4 wc

11 V 1 G 2 9 G wherein R33 represents alkyl of from C8 to C20, preferably CIO to C16;and ns, Π4, n5 represent the number of moles of ethoxylation in the formula and are when taken together about from one to fifty, preferablynve te fifteen); δ (m) formula XTV which is an alkoxylated primary fatty alcohcl, preferably Ethylan CPG 945 (the alkoxylated primary fattyalcohcl may be represented by the formula R— OtPO^ŒO^ 10 wherein R34 represents alkyl of from C8 to C18, preferably C13 to C15; EO is ethylene oxide; PO represents propylene oxide; ηθ is an integer offrom 6 to 50. preferably from 6 to 9; ηγ is an integer from 4 to 8, preferably 4.5 to 6;and 15 (n) mixtures thereof.

Most preferably the adjuvant is of the formula represented by

Improve® or Tergitol® 15-S-12.

More preferably the compound of the formula I is an agroncmically acceptable sait of 3,4,4-trifluoro-3-butene-l-amine, 20 preferably the monohydrochloride sait thereof; N-(3,4,4-trifluoro-3-bntenybglycine, preferably the monohydrochloride sait thereof; 2-aminO’N-(3,4,4-trifluoro-2-butenyl)propanamide, preferably themonohydrochloride sait thereof; (S)-2-amino-4-(methylthio)-N-(3,4,4-trifiuoro-3-butenyl)butanamide, preferably the monohydrochloride sait 25 thereof 4,4-difluoro-3-buten-l-amine, preferably the monohydrochloride sait thereof; 3,4,4-trifluoro-3-butenoic acid,preferably the sodium sait thereof; a combination of 3,4,4-trifluoro-3-butenoir acid and 3,4,4-trifluoro 3-buten-l-amine in a one to one ratio(1:;; .'S~2-aniino-3-hydroxy-N-(3,4,4-trifluoro-3-butenyl)butanamide, 30 preferably the monohydrochloride sait thereof; N-(4,4-difluoro-3-butenyl glycine, methyl ester, preferably the monohydrochloride saitthereof; a combination of 3,4,4-trifluoro-2-butenoic acid and 2-prepanamine in a one to one ratio (1:1); N-(3,4,4-trifluoro-l-oxo-3- 12 butenyl)glycine; 2-[(3,4,4-trifluoro-3-butenyl)amino]acetamide,preferably the monohydrochloride sait thereof; or 3,4,4-trifluoro-3-butenoic acid, 2-aminoeth.yl ester, preferably the monohydrochloridethereof. 5 More preferably the parasitically active ingrédient is 3,4,4- trifluoro-3-butene-l-amine, preferably the monohydrochloride saitthereof; or N-(3,4,4-trifluoro-l-oxo-3-butenyl)glycine and mostpreferably the active ingrédient is N-(3,4,4-trifluoro-l-oxo-3-butenyl)glycine. 10 It is surprising that a combination of a compound of the formula I and from about 0.05 to 20 % but less than an amount toxic toan infested plant, preferably about 0.10 to 2 %, of an adjuvant activeingrédient of the formula II, III, TV, V, VI or mixtures thereofincreases the effectiveness of the compound of formula I against 15 parasitic, particularly nematode infestation when applied to foliage ofthe infested plants by an unexpected différence compared to the acombination of the compound of formula I with other known surface-active wetting dispersing, and emulsifying agents commonly used inagricultural formulations. An ordinarily skilled artisan would be able 20 to fine the % of adjuvant effective for a particular compound of theformula. The percentage expressed is by volume.

Therefore, the présent invention is also a method forcontroliing nematodes, insects, and acarids and for the use of the novelcompositions for controliing nematodes, insects, and acarids 25 comprising treating an infestation of nematodes, insects, and acaridseither on the foliage or the soil of infested plants with a compound ofthe formula I together with an activity enhancing amount of anadjuvant of the formula II which is alkyl glycoside, preferably APG®325 or Atplus 258 in the amount of 0.25-1%; 30 an adjuvant of the formula III which is ethoxylated cocomethyl ammonium chloride, preferably Ethoquad C/12 in the amount of 0.25-l%h an adjuvant of the formula IV which is fatty amine ethoxylate,preferably Improve® in the amount of 0.25-2%; 13 ύ Hî 2 9 Ο an adjuvant of the formula V acetylenic diol ethoxylate, preferablySurfynol 485 and preferably in the amount of 0.5-1%; oran adjuvant of the formula VI an ethoxylated secondary alcohol,preferably Tergitol® 15-S-7 in the amount of about 0.5%, Tergitol® 15- 5 S-9 in the amount of about 0.5%, or Tergitol® 15-S-12 in the amount of0.5%.

Detailed Description of the InventionThe novel compositions of the présent invention are useful as an unexpectedly effective systemic composition for controlling 10 nematode, insect, and acarid infestation of a plant. These compositions provide a lower effective foliar use rate of compound offormula I while maintaining efficacy in nematode, insect, and acariddisease control. That is, when appîied to the foliage or stems of a plantthey are able to move through the phloem and xylem of the plant and 15 provide control of nematodes, insects, or acarids at other locations ofthe plant.

The présent methods for systemic control of nematodes,insects, and acarids use unexpectedly enhanced phloem mobilecompositions of the présent invention. These compositions having a 20 compound of Formula I and a sufficient amount of an adjuvant to unexpectedly provide enhanced effectiveness. It has been proposed theenhanced effectiveness of the présent compositions résulte fromimproved phloem mobility in order to relocate the compound ofFormula I downward in a plant without eliminating the nematode-, 25 insect- or acarid-controlling activity of the compound of Formula I.

To effectively control nematodes or other pests systemically by application to the above-ground surfaces of a plant, the présentcompositions may improve the active ingrédient capability of passingthrough the cuticle of the foliage or stem of a plant, passing into the 30 phloem, and remaining there long enough to be transported throughcut the plant so as to move to untreated areas including theroots. There such a compound of formula I may leak out or in someway contact the pests to such an extent that they are killed or repelledand the damage they would do to the plant is reduced or eliminated. 14 h: 290

During these steps throughout the plant, a compound of formula I mayundsrgo Chemical reactions, such as hydrolysis, or biologicalréactions, such as enzymatic actions. In addition, the formula I of thepressnt invention may be devised which, when placed on the plant,prior to absorption into the plant, may undergo reactions that resuit ina compound that is readily absorbable, translocatable, and effective inpreventing pest damage. An example of such compounds are thosehaving UY-labile protecting groups which when exposed to naturallight undergo reaction and resuit in active and mobile dérivatives ofcompounds of the formula I. Another example is silylated aminedérivatives.

Therefore, what is placed on the foliage or stem of the plantmay not be a composition wherein the compound of formula I isactually transported or the compound of formula I that actuallyControls the pest. Thus, the methods of the présent inventionprovice for compositions that may be transformed through Chemical orbiological reactions to hâve proper polarity for systemic activity.

Although the methods of the présent invention includeapplyimg composition to the plant locus, preferably to the foliage, areknown, the présent compositions are surprising combinations ofcompcunds of the formula I as defined above and selected adjuvants ofthe formulae II, III, IV, V, VI or mixtures thereof. Thesecombinations are for adjuvants that can not be predicted from amongthose commonly used in agronomics.

Among the compounds of the formula I, in order to controlmematodes it is preferred that n is 1 and X, Y,and Z are ah F, and Ql is then CH2NH3+W-, that is, a sait of 3,4,4-trifluoro-3-butene-l-amine. When Ql is CB^NHRg, Rg is preferably an alpha-amino acid linked by a peptide (amide) bond, morepreferably a protein amino acid. When Ql is (C=O)-R|j, Rjj is preferably hydroxvl and the compound is thus 3,4,4-trifluoro-3-butenoic acid or a sait thereof, including a sait formed with

V 15 3.4.4- trifluoro-3-butene-l-amine, that is, 3.4.4- crifluoro-3-butene- 1-amine 3,4,4-trifluoro-3-butenoate. W- may be any agronomically acceptable anion. 5 This includes, but is not limited to chloride, iodide,bromice, oxalate, sulfate, phosphate, citrate, acetate,or a flaoroalkene carboxylate, for example, F2C=CPCH2C00-.

In addition to the compounds specifically 10 described above, ail agronomically acceptable salts ofthe compounds are within the scope of the présentinvention. For example, a compound of the présentinvention having a free amine group may also exist asthe prcionated form having various anions associated 15 therewith, for example, but not limited to, chloride, bromide, iodide,phosphate, oxalate, sulfate, citrate,and acetate. In addition, aflaoroalkene carboxylate ion, such as F2C=CFCH2COO-, may be theco un ter-ion. A compound of the présent invention having a carboxylic 20 acid or hydroxyl group may exist as the sait havingvarious cations associated therewith, for example, butncr limcted to, alkali earth metals, such as sodium,calcium, and potassium; magnésium; or quaternaryammonium ions, such as ammonium, mono-, di-, or 25 trialkyLammonium, for example, isopropylammonium, orpyridinlum. In addition, a fluoroalkenyl ammonium ion,such as F2C=CFCH2CH2NH3+, may be the cation. Ail suchcompounds and others having similar characteristics,belng agronomically acceptable, are encompassed by the présent 30 invention.

As used herein, the term "halo", "halide", or "halogen"means Guorine, chlorine, iodine, or bromine or cognâtes thereof.

The term "alkyl" in the définitions of the formula I meansstraight-chain or branched groups of from one to about seven carbon 16 vt u290 atoms. The term "lower alkyl" means a such a group containing fromone to about four carbon atoms. The term "aliphatic" means saturatedor unsaturated, branched or straight-chain, alkyl groups having fromone to ten carbon atoms.

The term "alkoxy" means a lower alkyl group bonded via anoxygen atom. The term "alkylthio" means a lower alkyl group bondedvia a sulfur atom. The term "alkoxycarbonyl" means the lower alkylester of a carboxyl group.

The term "aliphatic amine" means an aliphatic groupwherein at least one hydrogen is replaced with -ΝΉ2· The term "aliphatic carboxylic acid, its esters, thiol esters, and amides" meansan aliphatic group wherein at least one carbon is a carboxylic group,-COOH, or is the lower alkyl ester, lower alkyl thiol ester, or amidethereof.

The term "aromatic group" or "aryl” means phenyl,optionally substituted with at least one group selected from hydroxy,alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl,and phenyl. It should be obvious to one of ordinary skill in the art thathetero cycles could also be used for the aromatic group, for example,thiadiazole, pyridine, thiazole, isothiazole, oxazole, pyrazole, triazole,benzothiazole, thiophene, furan, and the like, ail of which may also becptionally substituted.

As used herein, the phrase "amino acid amide of Q" (or Qj)means that is an amino acid coupled via a peptide (amide) bond tothe N GÎCH^NHRg. This amino acid may be a natural, i.e., protein,amino acid cr a nonnaturally occurring amino acid. The amino groupc: the amino acid may be a substituent of any carbon in the group, forexample, alpha, beta, or gamma to the carbonyl.

The term "alkyl or aryl hydrazine" means a hydrazine groupsubstituted with a lower alkyl or phenyl group, which in turn may beoptionally substituted. The term "alkyl or aryl sulfonamide” means asulfonamide group substituted with a lower alkyl or phenyl group,which in turc may be optionally substituted. 17 V 1U29 0

COMPOUNP SYNTHESIS

Methods of préparation for the compounds of formula I of theprésent invention are described in PCT application NumberPCT/US92/1474 which is incorporated by reference therefor.

FORMULATIONS

In normal use, the compositions usually will not be employedfree from further admixture or dilution, but ordinarily will be used in asuitable formulated composition compatible with the method ofapplication and comprising an effective amount of the composition.

The compositions of this invention may be blended with additionalagriculturally acceptable surface-active agents and carriers normallyemployed for facilitating the dispersion of active ingrédients,recognizing the accepted fact that the formulation and mode ofapplication may affect the activity of the composition. The présentcomposition may be applied, for example, as sprays, dusts, orgranules, to the area where pest control is desired, the type ofapplication varying with the pest and the environment. Thus, thecompositions of this invention may be formulated as granules of largeparticle size, as powdery dusts, as wettable powders, as emulsifiableconcentrâtes, as solution, and the like.

Granules may comprise porous or nonporous particles, suchas attapulgite clay or sand, for example, which serve as carriers forthe présent compounds. The granule particles are relatively large, adiameter of about 400-2500 microns typically. The particles are eitherimpregnated with the composition of the invention from solution orcoated with the composition, adhesive sometimes being employed.Granules generally contain 0.05-10%, preferably 0.5-5%, activeingrédient.

Dusts are admixtures of the compounds, with finely divided so'ids such as talc, attapulgite clay, kieselguhr, pyrophyllite, chalk, diatomaceous earths, calcium phosphates, calcium and magnésium carbonates, sulfur, flours, and other organic and inorganic solids which art as carriers for the compound. These finely divided solids 18 υ i ύ 2 9 0 hâve an average particle size ofless than about 50 microns. A typicaldust formulation contains 1 part of compound and 99 parts of talc.

The compositions of the présent invention may be made intoliquic. concentrâtes by dissolution or émulsification in suitable liquidsand into solid concentrâtes by admixture with talc, clays, and otherknown solid carriers used in the agricultural Chemical art. Theconcentrâtes are compositions containing about 5-50% activecomposition of which 98.00-99.25% may be of the formula I and 0.25- 2%may be adjuvant and 95-50% inert material, which includes surface-active dispersing, emulsifying, and wetting agents not within thecefiniùon of adjuvant herein, but even higher concentrations ofpesticidal active ingrédient or adjuvant active ingrédient may be emnloyed experimentally. The concentrâtes are diluted with wateror other liquids for practical application as sprays, or with additionalsolid carrier for use as dusts. A typical 50% wettable powder formulation would consist of50.0% 'wt/wt) of the composition, 22.0% attapuîgite diluent, 22.0% ofkaolin diluent, and 6.0% sodium salts of sulfonated Kraft ligninemulsifier.

Typical carriers for solid concentrâtes (also called wettablepcwders) include fuller's earth, clays, siiicas, and other highlyabsorbent, readily wetted inorganic diluents. A suitable solidccncenrrate formulation may contain 1.5 parts each of sodiumlignosudfonate and sodium lauryl sulfate as additional wetting agents,2c parts of active compound and 72 parts of attapuîgite clay.

Manufacturing concentrâtes are useful for shipping lowmelting products of this invention. Such concentrâtes are prepared bymelting the low melting solid products together with one percent ormcre of a solvent to produce a concentrate which does not solidify oncocling to the freezing point of the pure product or below.

Useful liquid concentrâtes include the emulsifiable concentrâtes, which are homogeneous liquid or paste compositions readily dispersed in water or other liquid carriers. They may consist entirely of the active compound with a liquid or solid emulsifying 19 Ο 1 G 2 9 0 agent, or they may also contain a liquid carrier such as xylene, heavyaromatic naphthas, isophorone and other relatively non-volatileorganic solvents. For application, these concentrâtes are dispersed inwater or other liquid carriers and normally applied as sprays to areasto be treated. A typical 50 gram per liter emulsifiable concentrateformulation would consist of 5.9% (wt/wt) of a composition of theinvention; as emulsifiers a 1.80% of a blend of the calcium sait ofdodecylbenzene sulfonate and nonionic 6-molar ethylene oxidecondensation product of nonylphenol, 2.70% of a blend of the calciumsait of dodecylbenzene sulfonate and a nonionic 30-molar ethyleneoxide condensation product of nonylphenol, 1.50% of a nonionic paste ofpolyalkylene glycol ether, and 88.10% refined xylene solvent.

Typical surface-active wetting, dispersing, and emulsifyingagents for use in formulations in addition to the adjuvants of theprésent invention are other agricultural formulations which include,for example,, the alkyl and alkylaryl sulfonates and sulfates and theirsodium salts; alkylamide sulfonates, including fatty methyl taurides;alkylaryl polyether alcohols, sulfated higher alcohols, polyvinylalcohols; polvethylene oxides; sulfonated animal and vegetabîe oils;sulfonated petroleum oils; fatty acid esters of polyhydric alcohols andthe ethylene oxide addition products of such esters; and the additionProducts of long-chain mercaptans and ethylene oxide. The surfaceactive agent normally comprises about 1-15% by weight of the activeingrédient. Thus, in the présent compositions the surface active agentin addition to the adjuvant of the présent invention composition mayreduce this percentage of other surface active agents used to formulatethis composition.

Other useful formulations include simple solutions of theinvention composition in a solvent in which it is completely soluble atthe desired concentration, such as water, acetone, or other organicsolvents- The preferred formulation for foliar application is anaqueous solution, more preferably containing a sufficient amount ofadjuvant, to provide an enhanced parasitically active compoùnd of the 20 O i (} 2 9 0 formula I as well as provide the desired concentration. However,glycerin and other surface active agents such as Tween®20, and mostpreferably 1% glycerin and 0.1% Tween®20 may also be part of theformulation. 5 The compositions may be formulated and applied with suitable pesticidal active ingrédients, including insecticides,acariddes, fungicides, plant regulators, herbicides, fertilizers, etc.

METHQPSQF-USE

The présent invention provides methods of controlling various 10 pests that prey on agricultural crops, namely nematodes, insects, andacarids. An infestation of a plant by any of these pests may becontrclled by applying to the plant locus an effective amount of any ofthe compounds of the présent invention. The application may be madein a variety of ways, including applying the compound or a composition 15 containing it to the soil before or after planting or emergence, to theseed or seed pièces prior to or at planting, and to the plant foliage,stems, or trunks. The treatment may be made more than once duringa growdng season with one or more days between treatments. Anappropriate treatment schedule will dépend on the life cycle of the pest 20 te be controlled, ambient températures, and moisture levels. Inadditicn the âge or size of the plant may influence the treatmentschedule.

The methods of the présent invention may be carcied out on avariety of crops. These include, but are not limited to, fruit and 25 vegetable crops, such as potatoes, sweet potatoes, carrots, tomatoes,grapes, peaches, citrus, bananas, corn, and soybeans; tobacco; andcottcn.

Compounds of the présent invention may be used to controlany of the phvtopathogenic nematodes. Insects which may be 30 controlled by the methods of the présent invention include, but are not limited to, foliar pests such as green peach aphids, and soil-bome pests such as Southern corn rootworm. Acarids which may be controlled by the methods cf the présent invention include, but are not limited to two spetted spider mites. Although no tests hâve been specifically 21 v à u 2 9 0 performed using the compositions tests conducted with a few of theparasitically active compounds of the présent invention revealed nosigniôcant level of control of tobacco budworm or Colorado potatobeetle. A preferred rate of application of a composition wherein thecompound of the formula I is enhanced by combination with from0.25% to 2% by weight of active adjuvant of the formula II, for examplein combination is found to be about 4 or 8 oz/acre to obtain levels ofcontrol (80-100%) that are comparable at 16 oz/acre with Triton CS7 forcontrol of root knot nematodes.

TKSTSUMHhPS

The following methods were used to evaluate adjuvants thatare ccmbined with a compound of formula I, speciôcally, for example,N-(3,4,4-trifluoro-l-oxo-3-butenyl)glycine. A track sprayer is used for foliar applications to approximateapplication procedures and volumes commonly used in the field ( 25gal/A). Twenty mis of each test solution is formulated in water,estimating that 10 mis would actually be applied to the 5 plants'treatment (5" or 6" round pots; soil mix: 50% Metromix, 25%fine sand, 25% medium sand , with 136 g Osmocote 14-14-14/0,3; one 3-4week old Rutger tomato plant/pot). Plants are often transplanted intothe 5" or 6" pots; at least one day is allowed between transplanting andtreatment. Pots are spaced along the track sprayer’s 5 ft long centerstrip. A single 8001E nozzle tip is placed in a boom directly over thepiants and adjusted to 6-9" above the leaf canopy. Pressure is set to15psi, resultdng in 4.2-4.5 ml/sec release. The track sprayer speed isadjusted to approximately 95 on the dial giving an LCD speed readoutof 1.75-1.85. Generally, tests are comprised of 20 treatments plus anumnoccilated control treatment.

After Chemical application, plants are allowed to dry for 2-4heurs and are then inoculated. 4-6 shahow holes are made in proximity to the plant stem using a thickpen, for the addition of Meloidogyne incognito (root knot) nematodeeggs. 30 mis of egg suspension (720 eggs/ml, 21,000 eggs/plant) are 22 distributed among ail holes in a pot using a large syringe. Plants arerandomized before inoculation and then moved to either Greenhouse 16or 21 for 3-4 weeks incubation. Greenhouse day températures are 25-30°C and supplémentai overhead light brought day length to 12 hours. Atévaluation, foliage is examined for phytotoxic effects and then stemsare eut to 1-2 inches above soil level. Excess soil is shaken from root bailand roots are washed free of soil mix using a high pressure waternozzle. Roots are evaluated for severity and quantity of galling visibleand eaeh replicate given a disease severity rating 0-100%. This data isentered into a SAS program and results are compared to both theinoculated control and (S)-2-amino-4-(methylthio)-N-(3,4,4-trifluoro-3-butenyDbutanamide, monohydrochloride, with Triton CS7 or (S)-2-amino-4-(methylthio)-N-(3,4,4-trifluoro-3-butenyl)butanamide,monohydrochloride, without adjuvant. Several commercial andexperimental adjuvants were tested and are listed below with theiraexive ingrédient and percentages identified as foliows: TABLE 1 Adjuvant %ai Active Ingrédient NH3SO4 1 00 ammonium sulfate ARG® 225 70 alkyl glycoside AP G® 300 50 alkyl glycoside ARG® 325 70 alkyl glycoside Arcuad T 127W 27 trimethyl tallow ammonium chloride Su’ferc. de 1 0 phosphoric acid Cayuse 42.5 + 16.5 phosphate ester of polyglycoethers ammonium salts Improve® 64 + 14 fatty amine ethoxylate ethoxylated nonylphenol 23 vl0290 5 10 15

CropOil 1 7 polyoxyethylated polyol fatty acid ester + polyol fatty acid ester Ethoquad C/25 1 00 cocomethyl 15EO ammonium chloride Ethoquad C/12 100 cocomethyl 2EO ammonium chloride Emcol® CC9 100 propoxyiated quaternary amine Glycerin 100 glycerin MON 0818 1 5 polyoxyethylene alkyl (tallow) amine Nitrogen 28 28% nitrogen nonyiphenol 4EO 1 00 nonyiphenol 4EO nonyiphenol 6EO 100 nonyiphenol 6EO nonyiphenol 8EO 100 nonyiphenol 8EO nonyiphenol 10EO 1 00 nonyiphenol 10EO nonyiohenol 12EO 1 00 nonyiphenol 12EO R-11 90 octyl phenoxy éthanol Silwe* L77 100 organosilicone ethoxylate Surfynol 465 100 10 mole EO acetylenic diol ethoxylate Surfynol 485 1 00 30 mole EO acetylenic diol ethoxylate p"ergi:ol® 15-S-3 100 C11-C15 secondary alcohol EO Tergiroi® 15-S-5 1 00 C11-C15 secondary alcohol EO Tergiroi® 15-S-7 1 00 C11-C15 secondary alcohol EO Tergitol® 15-S-9 100 C-j-i-C-15 secondary alcohol EO 20 ΤΑ v i ί; 2 9 Ο

Tergitol® 15-S-12 1 00 secondary alcohol EO Tergitol® 15-S-15 100 θ11"θ15 secondary aicohol EO Tween 20 1 00 polyoxyethyiene (20) sorbitan monolaurate Triton® CS-7 60 alkyl aryl polyethoxylate and sodium sait of alkyl sulfonated alkylate Varion CDG-K 28 lauryl betaine

The following results using the above methods show compoundsof the formula I, ie 2-amino-N-(3,4,4-trifluoro-2-butenyl)propanamide,monohydrochloride sait (denoted as A hereinafter), (S)-2-amino-4- 10 (methylthio)-N-(3,4,4-trifluoro-3-butenyl)butanamide, monohydrochloride sait (denoted as B hereinafter), 3,4,4-trifluoro-3-butenoic acid, sodium sait (denoted as C hereinafter), N-(3,4,4-trifluoro-l-oxo-3-butenyl)glycine(denoted as D hereinafter), 2-[(3,4,4-trifluoro-3-butenyl)amino]acetamide, monohydrochloride sait (denoted 15 as E hereinafter), 3,4,4-trifluoro-3-butenoic acid, 2-aminoethyl ester,monohydrochloride sait (denoted as F hereinafter), thereof that theselected adjuvants of the présent invention combination provide anunexpected enhancement of the compound of the formula I. (*FOR I) 25 TABLE 2cont’d FOR 1* Adjuvant Adj% 1 6 8 4 2 B no adj 35 38 B no adj 2 9 1 9 B no adj 28 1 3 B no adj 35 22 B no adj 38 24 B no adj 24 9 B no adj 1 9 6 B NH3SO4 2 22 9 B APG® 225 .25 59 1 4 B APG® 225 .25(ai) 47 9 B APG® 225 .5 62 36 B APG® 225 1 56 34 B APG® 225 1 (ai) 88 49 B APG® 300 .25 37 16 B APG® 300 ,25(ai) 58 7 B APG® 300 .5 73 1 9 B APG® 300 1 67 40 B APG® 300 1 (ai) 92 55 B APG® 325 .25 88 49 B APG® 325 .25(ai) 64 9 B APG® 325 .5 74 6 9 B APG® 325 1 70 29 B APG® 325 1 (ai) 96 47 B Arquad T .25(ai) 31 2 B Buffercide .25 1 2 8 B Cayuse .25 41 21 B Cayuse .75 47 27 B CrooOil .5 43 1 8 B CroDOil 2 30 25 B CS7 .5 28 7 B CS7 .5 98 33 3 B CS7 .5 81 28 1 3 B CS7 .5 81 24 1 1 B CS7 .5 92 62 21 B CS7 .5 51 1 8 9 26

t b 2.9 C 5 10 15 20 25 30 B OS7 .5(ai) 95 58 21 B CS7 .5(ai) 93 63 54 B CS7 • 5(ai) 1 00 81 21 B CS7 .5(ai) 50 1 1 B CS7 :5(aj). 55 1 5 B CS7 • 5(ai) 55 1 3 B CS7+NH3SO4 .5+2 23 14 B CS7+28%N .5+2 17 8 B CS7 .5 90 40 B Emcol® CC9 1 5 5 B Emcol® CC9 5 1 8 5 B Ethoquad 0/12 .25 91 B Ethoquad C/12 ,25(ai) 67 1 6 B Ethoquad C/12 .5 91 B Ethoquad C/12 1 98 B Ethoquad C/12 1 (ai) 79 50 B B Ethoquad C/25 1 21 8 B Ethoquad C/25 5 38p 28 B Ethoquad C/25 2.5(ai) 36 1 1 B Ethoquad C/25 1 +Surfynol 465 .5(ai) 62 26 C Glycerin 1 (ai) 82 4 0 D Glycerin 1 (ai) 61 27 B Imqrove® .25 7 3 1 0 B ImDrove® .25 1 00 7 3 1 5 B Imqrove® .5 80 23 B Imqrove® .5 93 30 B Imqrove® .5 1 00 98 28 B Imqrove® ,5(ai) 94 56 B Imqrove® .5(ai) 9 6 62 B ilmprove® ,5(ai) 9 3 34 B îlmqrove® 1 80 20 B limqrove® 1 1 00 91 28 3 Ilmprove® 1 (ai) 99 74 B Ilmqrove® 2 9 1 46 B Ilmqrove® 2 83 38 B Ilmqrove® 2 1 00 88 48 B Ilmqrove® ,5(ai) 35 27 c 2 9 Ο +glycerin 1 (ai) 73 3 7 E Improve® .5(ai) 97 93 E Improve® • 5(ai) 97 8 6 54 C Improve® ,5(ai) 1 00 9 9 93 c Improve® • 5(ai) 97 97 c Improve® 5(ai) 1 00 83 38 c Improve® • 5(ai) +glycerin Hai) 68 44 D Improve® ,5(ai) 1 00 99 92 TABLE 2 cont’d ‘FOR 1 Adjuvant A d j % 1 6 8 4 2 D ImDrove® .5(ai) 100 96 D ImDrove® • 5(ai) 92 37 21 D ImDrove® .5(ai) +glycerin 1 (ai) 88 80 51 A ImDrove® .5(ai) 97 8 8 59 F ImDrove® .5 1 00 8 7 F ImDrove® .5(ai) 1 9 F ImDrove® •5(ai) 76 46 F ImDrove® 1 1 00 9 4 B MON 0818 .25 42 26 B MON 0818 .25 6 9 22 B MON 0818 1 35 1 3 B 28% N 42 6 B 28% N 2 5 6 1 2 B nonylphenol 4EO .5(ai) 1 1 9 B nonylphenol 6EO ,5(ai) 20 1 8 B nonylphenol 8EO • 5(ai) 29 4 B nonylphenol 10EO .5(ai) 1 8 8 B nonylphenol 12EO .5(ai) 38 9’ B R-1 1 .06 33 1 3 B R-1 1 .25 28 1 0 B ISilwet L77 ,25(ai) 22 1 1 B Silwet L77 .5 24 1 5 B Silwet L77 1 1 8 23 IB ISilwet L77 2 23p _ 27 V» G 2 9 Ο +glycerin 1 (ai) 73 3 7 - Improve® .5(ai) 97 93 E IrriDrove® .5(ai) 97 8 6 54 C ImDrove® .5(ai) 100 9 9 93 0 IrriDrove® .5(ai) 9’7 97 C Improve® .5(ai) 1 00 83 38 c ImDrove® .5(ai) +glycerin 1 (ai) 68 44 D Imorove® .5(ai) 100 99 92 TABLE 2 cont’d *FOR 1 Adjuvant Ad j % 1 6 8 4 2 D ImDrove® .5(ai) 1 00 96 D ImDrove® .5(ai) 92 37 21 D ImDrove® .5(ai) +giycerin 1 (ai) 88 80 51 A Imorove® .5(ai) 97 8 8 59 F Improve® .5 1 00 8 7 F ImDrove® • 5(ai) 1 9 F Improve® .5(ai) 76 46 F ImDrove® 1 1 00 9 4 B MON 0818 .25 42 26 B MON 0818 .25 6 9 22 B MON 0818 1 35 1 3 B 28% N 42 6 B 28% N 2 5 6 1 2 B nonylphenol 4EO .5(ai) 1 1 9 B nonylphenol 6ΞΟ •5(ai) 20 1 8 B nonylphenol 8EO •5(ai) 29 4 B nonylphenol 10EO .5(ai) 1 8 8 B nonylphenol 12EO • 5(ai) 38 9 B |R-11 .06 33 1 3 B ÎR-11 .25 28 1 0 B ISilwet L77 ,25(ai) 22 1 1 B jSilwet L77 .5 24 1 5 B ISilwet L77 1 1 8 23 B ÏSilwet L77 2 23p _ υ u; 2 9 0 28 B Silwet L77 5 62p 26p B Silwet L77 5 48p 32p B Silwet L77 .25 TABLE 2cont’ d *FOR I Adjuvant Adj % 1 6 8 4 2 +MON 0818 .25 5 4 22 B Silwet L77 .5 +MON 0818 .25 4 7 1 8 B Surfynol 465 1 1 8 15 B Surfynol 465 5 33p 5p B Surfynol 485 .25(ai) 6 7 1 1 B [Surfynol 485 ,25(ai) 5 7 14 B [Surfynol 485 • 5(ai) 8 3 13 B [Surfynol 485 1 (ai) 7 1 30 B SSurfynol 485 1 (ai) 92 51 B ÏTergitol® 15-S-3 ,5(ai) 49 7 B ÏTergitol® 15-S-5 .5(ai) 51 21 B ÏTergitol® 15-S-5 .5(ai) 40 0 B ÏTergitol® 15-S-7 ,5(ai) 86 49 B ÏTergitol® 15-S-7 j(ai) 74 26 Γ ÏTergitol® 15-S-7 ,5(ai) 35 3 ÏTergitol® 15-S-9 .5(ai) 90 23 3 ÏTergitol® 15-S-9 ,5(ai) 91 5 8 3 ÏTergitol® 15-S-12 .5(ai) 8 8 9 3 ÏTergitol® 15-S-12 .5(ai) 100 78 3 ÏTergitol® 15-S-12 • 5(ai) 96 58 3 (Tergiîol® 15-S-12 .5(ai) 96 60 3 Tergiîol® 15-S-12 .5(ai) 83 54 C Tergiîol® 15-S-12 .5(ai) 97 76 C Tergiîol® 15-S-12 -5(ai) 97 80 37 29 </Hî 2 9 0 c Tergitol® 15-S-12 ,5(ai) +glycerin 1 (ai) 91 68 29 TABLE 2 cont’d *FOR ï Adjuvant Adj % 1 6 8 4 2 D Tergitol® 15-S-12 ,-5(a») 99 88 D Tergitol® 15-S-12 ,5(ai) 96 88 43 D Tergitol® 15-S-12 +glycerin 1 (ai) 95 55 B Tergitol® 15-S-15 •5(ai) 67 49 B Tergitol® 15-S-15 ,5(ai) ... 7 4 5 B Tween 20 .25 36 7 B Varion ,25(ai) 47 0 p = phytotoxicity noted on foliage

Boldface % control indicates statistically signifîcant improvement indisease control compared to I-B, at the same rate, with either no adjuvantor Triton CS7, in the same test. Adj. % is as defined in Table I, except (ai)in the % Adj column means the volume of adjuvant noted in Table I isadjusted for the concentration of adjuvant active ingrédient.

The surface-active or metting agents identified above are sold underthe noted names as follows. APG® is sold by Henkel APG, Arquad is soldby Akzo, Chemical Division, Bufiercide is sold by Custom Chemicals.Cayuse® is sold by Wilbur-Ellis Co. Improve® is sold by Dow-Elanco.CropOil is available from various sources. Ethoquad is also sold by Akzo,Chemical Division, Emcol is available from Witco Coip. Organics Div.,28% Nitrogen can be made from usual nitrogen containing compounds.Nonylphenol is sold by, for example, Witco S.A, R-1I is available fromWilbur-Ellis Co. Silwet is from Union Carbide Corp., Spécial ChemicalsDiv. Surfynol is a product of Air Products and Chemicals, Inc. Tergitol is 30 <, ni 2 9 0 also a product of Union Carbide Corp., Industrial Chemicals Div. Tween20 is from ICI Americas, Inc. Triton® is from Rohm and Haas Co.

Varion is from Sherex Chemical Co., Inc.

The following methods are also used to evaluate adjuvants that arecombined with a compound of formula I, specifically, for example,N-(3,4,4-trifluoro-1 -oxo-3-butenyl)glycine, for effectiveness incontrolling root knot nematodes (Meloidogyne incognito,) on tomato rootswhen the adjuvant plus compound mixture is applied to the foliage ofyoung plants.

Tomato plants (cultivar 'Rutgers') were grown one per pot in six cmsquare plastic pots containing a mixture of equal parts fine sand, coarsesand, silt loam soil, and commercial potting medium.

Compound/adjuvant mixtures were prepared by adding the compound towater to achieve final concentrations of 2400, 1200, and 600 ppm, and thenadding the adjuvant to the solution to achieve a final concentration of 0.5%volume of adjuvant/volume of water. This single adjuvant concentrationwas used with ail 3 rates of the test compound, unless otherwise specified.

When the tomato plants were 18-21 days old the test solutions weresprayed onto the leaves and stems using a track sprayer whichapproximates application procedures and volumes used in the field. Thetrack sprayer is calibrated to apply the test solution at a volume of 25gallons per acre, resulting in application rates of the compound of 8, 4,and 2 ounces active ingrédient per acre. Three plants were sprayed foreach treatment and then were air dried and kept under fluorescent lightsfor 15-18 hours prior to inoculation. Ail plants then were inoculated withmature root knot nematode eggs containing J1 larvae, with 8,000 eggs perplant applied in 5 ml of water onto soil at the stem base. Plants then wereincubated in a growth chamber at 27C and 60% RH with ail replicate potsrandomized throughout the chamber. During the two weeks immediatelyfollowing application of the test mixtures ail plants received sub-irrigationand the foliage was kept dry. 31 ν Πΐ 2 9 Ο

Three to 7 days after treatment the plant foliage was examined forsymptoms of phytotoxicity and assigned a rating value of 0-3 where 0= nodamage, 1= mild spotting or chlorosis, 2= moderate damage but nostunting, and 3= severe damage and stunting. After three weeks 5 incubation as described above the plant roots were washed and nematodedisease severity was assessed. Each root System was rated individuallyand a visual estimate of the percent of the root System damaged bynematode galling was determined and assigned a value of 0, 1, 3, 5, 10, 25,50, 75 or 100% root damage. 10 32 ν ί υ 2 9 0 ADJUVANTS TESTED trede ρβπΐ£- Chemical name . ... concentration Atplus 258 alkylpolyglucoside 62% a.i. CS-7 alkyl aryl polyethoxylate and Na sait alkyl sulfonated alkylate 60% a.i. Dodigen 226 cocoalkyldimethyl benzyl ammonii chloride 50% a.i. Dodigen 4022 Emcol XE 1656 alkoxylated fatty amine oxide 70% a.i. Empigen OB alkyldimethyl amine oxide 30% a.i. Ethylan CPG 945 modified alcohol alkoxylate 100% a.i. Flo-Mo 3153 ethoxylated fatty amine oxide 70% a.i. Genapol T250 fatty alcohol polyglycol ether 100% a.i. Improve fatty amine ethoxylate 64% a.i. + ethoxylated nonylphenol 14% a.i. Kacmul 230 coco esterfied polyethoxyether 100% a.i. piperonyl butoxide 100% a.i. Rhodonat LMO coconut oil based sucroglyceride 100% a.i. Rhodonat MLP704 modified LMO sucroglyceride 100% a.i. Simusol M52 stearic acid polyethoxylated 100% a.i. Ethoduomeen ethoxylated alkyl amine 100% a.i. Ethomeen C-15 ethoxylated alkyl amine diamine 100% a.i.

MANUFACTUREES OF ADJUVANTS TESTED

Atplus 25STriton CS-7Dodigen 226Dodigen 4022Emcol XE 1656Empigen OB

Impérial Chemical IndustriesRohm &. Haas Co.

Hoechst AG

Witco Corp.

Albright & Wilsons 33 υ Μί 2 1) 0

Ethylan CPG 94 Harcros Chemicals Inc. Πο-Μο 3153 Witco Corp. Genapol T250 Hoechst AG Improve DowElanco Kaomul 230 KAO Spain piperonyl butoxide Fluka Chemika Rhodonat LMO Rhone-Poulenc Rhodonat MLP704 Rhone-Poulenc Simusol M52 Seppic France Ethoduomeen AKZO Corp. Ethomeen C-15 ALZO Corp. 34 010290

Table 3. Mean percent root damage due to nematode gallii-g (%disease), the standard déviation of that mean (std dev)„ the ‘S ccntrol ofroot damage (% control), and foliar phytotoxicity rating: (0=no phyzo,3=severe phyto) after treatment of tomato plants with (MON 4-5700 ' 5 mixed with the indicated adjuvants.

Adjuvant (0.5% v/v unless noted) D aai/ha % disease % contrcl prytcacx average average std dev CS-7 560 33.33 11.79 50.00 1.6' 280 66.67 11.79 0.00 1.00 Improve 560 20.00 7.07 70.00 2.00 280 28.33 16.50 57.50 1.0 0 140 58.33 11.79 12 50 0.6' Witco C5867 560 20.00 7.07 70.00 1.33 280 50.00 20.41 25.00 0.60 140 50.00 0.00 25 00 1.33 Dodigen 226 560 20.00 7.07 70.00 2.6? 280 41.67 11.79 37..50 2.6? 140 33.33 11.79 50. 00 2.33 Neodol 25-9 560 20.00 7.07 70..00 1.6? 280 58.33 11.79 12-50 1.33 140 58.33 11.79 12.50 0.6' Stepwet DF-90 560 20.00 7.07 70..00 1.6? 280 41.67 11.79 37-50 0.33 140 58.33 11.79 12.50 0.33 Emcol XE 1656 560 41.67 11.79 37,50 1.00 280 58.33 11.79 12-50 1.6? 140 66.67 11.79 0.00 1.00 Simusol M52 560 41.67 11.79 37-50 0.6? 280 66.67 11.79 0.00 0.33 140 66.67 11.79 0.00 0.6' CS-7 560 15.00 7.07 77.50 2.00 280 33.33 11.79 50. 00 0.6' Improve 560 6.00 2.94 91.00 2.6? 280 15.00 7.07 77.50 2.33 140 41.67 11.79 37 50 1.6? Ethylan CPG945 560 13.33 8.50 80.00 3.00 280 41.67 11.79 37.50 ί 2.33 140 58.33 11.79 12.50 ' 2.00 Rhodonat MLP704 560 8.33 2.36 87.50 2.6? 280 33.33 11.79 50.00 j 1.33 140 58.33 11.79 12.50 ! 0.6? ! L 35 G Πί 2 9 Ο

Adjuvant (0.5% vtv unless noted) D oai/ha % disease % control phytotox average average std dev Rhodon2t LMO 560 33.33 11.79 50.00 1.33 280 58.33 11.79 12.50 0.67 140 66.67 11.79 0.00 0.33 Kaomul 230 560 15.00 7.07 77.50 1.67 280 33.33 11.79 50.00 1.33 140 62.50 12.50 6.25 0.67 GenapoIT 560 5.00 0.00 92.50 2.67 280 15.00 7.07 77.50 1.67 1 40 41.67 11.79 37.50 0.67 Aîplus 258 560 6.00 2.94 91.00 1.67 280 10.00 0.00 85.00 0.67 1 40 41.67 11.79 37.50 0.67 CS-7 560 4.33 0.94 93.50 1.00 280 15.00 7.07 77.50 0.67 Improve 560 1.67 0.94 97.50 1.67 280 6.00 2.94 91.00 2.00 1 40 28.33 16.50 57.50 1.67 Flomo 3153 560 2.00 2.16 97.00 2.00 280 6.67 2.36 90.00 0.67 140 33.33 11.79 50.00 0.00 Ettiomeen C15 0.3% + 560 0.33 0.47 99.50 3.00 Tergitol 15S9 0.2% 280 3.33 2.36 95.00 2.67 1 40 41.67 11.79 37.50 2.00 Ethoduomeen T25 560 1.00 0.00 98.50 2.00 280 8.33 2.36 87.50 2.33 140 41.67 11.79 37.50 1.33 Ethomeen C15 0.18% + 560 11.67 9.43 82.50 2.67 Tergitol 15S12 0.12% +Tergitol 15S9 0.2% 280 0.00 0.00 100.00 3.00 140 0.00 0.00 100.00 3.00 Tergitol 15S9 280 0.00 0.00 100.00 3.00 140 0.00 0.00 100.00 3.00 Empigen OB 560 3.00 0.00 95.50 2.67 280 11.67 10.27 82.50 2.67 140 33.33 11.79 50.00 1.67 CS-7 560 3.67 1.89 92.67 1.67 280 8.33 2.36 83.33 1.33 36 υ i 0 2 9 0

Adjuvant fO.5% v-v unless notedi D aai/ha % disease % convoi phytotox average stddev average improve 560 280 140 0.33 6.67 15.00 0.47 2.36 7.07 99.33 86.67 70.00 2.00 1.33 1.00 Atblus 253 0.4% + prperonyi butoxide 0.1% 560 280 140 1.33 5.00 6.67 1.25 0.00 2.36 97.33 90.00 86.67 0.67 0.33 1.00 Atoius 253 0.5% + ammonium sulfate 2.0% 560 280 140 0.00 2.33 15.00 0.00 0.94 7.07 100.00 95.33 70.00 1.33 0.67 0.67 Ardus 253 0.5% 560 280 140 0.33 3.00 20.00 0.47 0.00 7.07 99.33 94.00 60.00 1.33 1.00 0.33 Irrprove C.5% + ammonium surate 2.3% 560 280 140 1.33 3.3325.00 1.25 2.36 0.00 97.33 93.3350.00 2.33 1.331.00 Improve C.5% + piperonyl butoxide C.1% 560 280 1 40 3.67 8.33 41.67 0.94 2.36 11.79 92.67 83.33 16.67 1.67 2.00 1.00 CS-7 0.5% + piperonyl butoxide C.1% 560 280 140 2.33 6.67 41.67 0.94 2.36 11.79 95.33 86.67 16.67 1.00 1.67 0.67 CS-7 560 280 6.67 28.33 2.89 20.21 87.00 43.00 2.33 1.33 imo’ove 560 280 140 6.00 15.00 41.67 3.61 8.66 14.43 88.00 70.00 17.00 1.67 1.33 0.67 Doc:gen 4C22 560 280 140 6.00 13.33 41.67 3.61 10.41 14.43 88.00 73.00 17.00 1.67 1.67 1.00 Docgen 4C22 0.4% -r Tween 20 :.i% 560 280 140 5.00 15.00 41.67 0.00 8.66 14.43 90.00 70.00 17.00 2.00 1.33 1.33 37 v ! C 2 9 Ο

Adjuvant <0.5% v/v unless noted) D aai/ha % disease % control phytotox average average std dev Dodigen 4022 0.32% + 560 13.33 10.41 73.00 2.00 Tween 20 0.08% + piperonyl butoxide 0.1% 280 41.67 14.43 17.00 1.33 140 58.33 14.43 -17.00 1.00 Tergitoi 15-S-9 0.2% 560 6.67 2.89 87.00 2.00 280 20.00 8.66 60.00 1.33 J 4P 41 .67 14,43 17.00 2.00 Eînomeen C15 0.15% + 560 5.00 0.00 90.00 1 .67 Tergitol 15-S-9 0.1% 280 1 5.00 8.66 70.00 1 .33 140 41.67 14.43 17.00 1 .00 Crop Life 5.0% 560 8.33 2.89 83.00 1 .67 280 25.00 0.00 50.00 0.67 1413 5Q.0P -O..Q CL£-Q., 1 .00 15 20

Claims

38 U G 2 9 Ο CLAIMS

1. A composition comprising a combination of a compound of the formula (I) 5 X \-Ç-(CH2)n- QY Z 10 I wherein: n = 1, 3, 5, 7, 9, or 11; Q is CH2NHE€, CH2NO2, CH2N=CHR2, CH2N=C=O, CH2N+R3R4R5W’,or (C=O)-Rn; 15 X, Y, and Z are independently H or F, provided that at least oce of X and Y is F, and further provided that when Q is (C=O)-Rueach of X, Y, and Z is F; W* is an agronomically acceptable anion; R2 is an aromatic group; 20 each of R3. R4, and R5 is independently hydrogen; a lower alkyl group, optionally substituted with at least one group selected fromhydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxy-carbonyl, and phenyl; one of R3, R4, and R5 is hydroxy and the other twoare hydrogen; or R3, R4, and R5 taken together with the nitrogen of Q 25 form a cvclic quatemary ammonium group; R^ is hydrogen; an aliphatic group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo,nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; anamino acid amide of Q; (C=O)-R7; CpCi2 aliphatic amines, optionallysubstituted with at least one group selected from hydroxy, alkoxy, halo, 30 39 U 1 G 2 9 0 nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; C2-C12 aliphatic carboxylic acids, their esters, thiol esters, and amides, ail optionally substituted with at least one group selected from hydroxy,alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, andphenyl; dihydro-3-oxo-pyrazolidinyl; or phenyl or thiophene, optionallysubstituted with at least one group selected from hydroxy, alkoxy, halo,nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;or Κθ taken with the nitrogen of Q is guanidine; hydrazine; alkyl or aryl hydrazine, optionally substituted with at leastone group selected from hydroxy, alkoxy, halo, nitro, amino, thiol,alkylthio, carboxyl, alkoxycarbonyl, and phenyl; or an alkyl or arylsulfonamide, optionally substituted with at least one group selectedfrom hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl,alkoxycarbonyl, and phenyl; R7 is (C=O)-Rj4; CpCi2 aliphatic group optionally substituted with at least one group selected from hydroxy, alkoxy, halo,nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; C2-C12 aliphatic carboxylic acid, esters, thiol esters, or amides thereof, ail optionally substituted with at least one group selected from hydroxy,alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl,and phenyl; or a N, O, or S group such that when taken with thecarboxamide is a urea, semicarbazide, carbamate, or thiocarbamategroup, ail optionally substituted with an alkyl or aryl group, optionallysubstituted with at least one group selected from hydroxy, alkoxy, halo,nitro, amino, thiol, alkylthio, carboxyl, alkoxy-carbonyî, and phenyl; R11 is -OR12, -SR12- halogen, -NHOH, or -NR12R13;each of R^2 ^13 independently hydrogen; an aliphatic or an aromatic group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl; a C1-C12 aliphatic 40 ι G 29 0 amine, optionally substituted with at least one group selected fromhydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl,alkoxycarbonyl, and phenyl; a C2-C12 aliphatic carboxylic acid, esters,amides and salts thereof, optionally substituted with at least one groupselected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio,carboxyl, alkoxycarbonyl, and phenyl; or R12 an^ R13 taken together with the N of Ru are a protein amino acid or a cyclic group selected from morpholine,piperidine, piperazine, or pyrrolidine, optionally substituted with atleast one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol,alkylthio, carboxyl, alkoxycarbonyl, and phenyl; R14 is OH, alkoxy, NH2, or NHNH2; or any agronomically acceptable sait thereof; together with or in combination with (a) formula II which is alkyl glycosides wherein the alkyl group is amixture of from about eight to about fourteen carbons and the number ofglycoside groups présent in the formula are from one to about six; (b) formula III which is a quaternized fatty amine ethoxylate whereinthe fatty amine is an alkylamine wherein the alkyl group is a mixture offrom about eight to about twenty carbon atoms, inclusive, and theethoxylate is an ethylene oxide monomer from about two to about fourteenmoles of ethoxylation; (c) formula IV which is a mixture of (i) a fatty amine ethoxylatewherein the fatty amine is an alkylamine wherein the alkyl group is amixture of from about six to about thirty carbon atoms, inclusive, and theethoxylate is an ethylene oxide monomer of from one to about fîfty moles ofethoxylation and (ii) ethoxylated alkylphenol wherein the alkyl is of fromzéro to about twenty carbons, inclusive, the ethoxylate is an ethylene oxidemonomer of from about two to about twenty moles of ethoxylation; (d) formula V which is ethoxylated acetylated diols wherein thenumber of carbons in the acetylated chain is of from ten to twelve carbon 41 b À G 2 9 0 atoms, inclusive, and the ethoxylate is an ethylene oxide monomer offrom ten to about thirty moles of ethoxylation; (e) formula VI which is a secondary alcohol or ethoxylate whereinthe ethoxylate is of from seven to fifteen, inclusive, of an ethylene oxidemonomer and the alkyl of the secondary alcohol or ethoxylate is of fromabout seven to about fifteen, inclusive; (f) formula VII which is an alkoxylated fatty amine oxide whereinthealkyls are of from about six to thirty carbons, inclusive; and thenumber of moles of alkoxylation are when taken together about fromone to fifty; (g) formula VIII which is an alkyldimethyl amine oxide whereinthe alkyls are of from about six to thirty carbons; (h) formula IX which is a fatty alcohol polyglycol ether wherein thefatty alcohol represents a mixture of alkyls of from about six to thirtycarbons, inclusive; and the number of moles of ethoxylation are whentaken together about from one to fifty; (i) formula X which is a coco esterified poîyethoxyether wherein thecoco ester represents a mixture of alkyls of from about six to thirtycarbons, inclusive; and the ethoxylation is from one to fifty; (j) formula XI which is a quaternary ammonium including an alkylof from C8 to C20 and an agronomically acceptable anion; (k) formula XII which is a quaternary ammonium having groupswhich are independently alkyl of from one to three carbons andtogether are from two to seven carbons; and of from three to fifteenethylene oxide and propylene oxide groups and an agronomicallyacceptable anion; (l) formula XIII which is diamine ethoxylate with an alkyl of fromC8 to C20 and ethoxylation of from about from one to fifty; (m) formula XIV which is an alkoxylated primary fatty alcohol withan alkyl of from C13 to C18 and of from 6 to 50 propylene oxide groups;and (n) mixtures thereof.

2. A composition of claim 1 wherein the compound of the formula I isan agronomically acceptable sait of 3,4,4-trifluoro-3-butene-l-amine, or 42 υ Μ.' 2 δ 0 the monohydrochloride sait thereof; N-(3,4,4-trifluoro-3-butenyl)glycineor the monohydrochloride sait thereof; 2-amino-N-(3,4,4-trifluoro-2-butenyl)propanamide or the monohydrochloride sait thereof; (S)-2-amino-4-(methylthio)-N-(3,4,4-trifluoro-3-butenyl)butanamide or themonohydrochloride sait thereof; 4,4-difluoro-3-buten-l-amine or themonohydrochloride sait thereof; 3,4,4-trifluoro-3-butenoic acid or thesodium sait thereof; a combination of 3,4,4-trifluoro-3-butenoic acid and 3.4.4- trifluoro-3-buten-l-amine in a one to one ratio (1:); (S)-2-amino-3-hydroxy-N-(3,4,4-trifluoro-3-butenyl)butanamide or themonohydrochloride sait thereof; N-(4,4-difiuoro-3-butenyl)glycine,methyl ester, or the monohydrochloride sait thereof; a combination of 3.4.4- trifluoro-2-butenoic acid and 2-propanamine in a one to one ratio(1:1); N-(3,4,4-trifluoro-l-oxo-3-butenyl)glycine; 2-[(3,4,4-trifluoro-3-butenyl)amino]acetamide or the monohydrochloride sait thereof; or 3.4.4- triiluoro-3-butenoic acid, 2-aminoethyl ester or the monohydrochloride thereof.

3. A composition of Claim 1 wherein the adjuvant is (a) the alkyl glycosides of the formula II wherein the alkyl group isa mixture of from about nine to eleven carbons, inclusive, and thenumber of glycoside groups présent in the formula are from one to two; (b) the quaternized fatty amine ethoxylate of the formula IIIwherein the alkyl group of the fatty amine is a mixture of from eight tosixteen carbon atoms and the number of moles of ethoxylates is two; (c) the mixture of the formula IV is (i) the fatty amine ethoxylate ofthe formula ^/(EO)nHRonN _ (EO)mH wherein: 43 v H! 2 9 Ο ^22 represents a mixture of alkyls of from about twelve to twentycarbons, inclusive; EO is an ethylene oxide monomer and n and mrepresent the number of moles of ethoxylation in the formula and arewhen taken together about from five to fifteen, and (ii) the ethoxylated 5 alkylphenol is the formula

wherein: 10 R 23 is a mixture of alkyl groups of from about eight to ten carbons; EO is the ethylene oxide monomer and w is the number of moles ofethoxylation in the formula and is from about six to ten moles; (d) the ethoxylated acetylated diols of the formula V is of formula

I I (EO)q (ÉO)P 15 wherein: ’ is a number of carbons to provide a total number of carbons in thechain of from 10 through 12 carbons, inclusive; EO is ethylene oxidemonomer wherein q and p represent the number of moles ofethoxylates in the formula and are when taken together 30; 20 (e) the secondary alcohol ethoxylate of the formula VI is wherein:

R24arepresents hvdroxy or an ethylene oxide monomer wherein a represents the number of moles of ethoxylate présent in the. formula 44 and is from nine to twelve, inclusive, and C* represents the ends of thecarbon cham such that altogether the chain is a mixture of carbonshavinc a total of from twelve to fourteen carbons, inclusive; zf) formula VII which is an alkoxylated fatty amine oxide, S including ethoxylated fatty amine oxide, (the alkoxylated fatty amine oxide is represented by theformula W 0- R' R25— |ψ — (CHCH2O)Zl-H I I (CHCH2O2)2 — h R' wherein R25 represents a mixture of alkyls of from about six to thirtycarbons inclusive, oreferably from about twelve to twenty carbons, 20 inclusive R is hydrogen or methyl: and z and z. represent the number of moles of alkoxylation or preferablyethoxylaoon m the formula and are when taken together about fromone to firty. preferably five to fifteen); 2> (s formula VIII which is an alkyldimethyl amine oxide, (the alky dimecnyl amine oxide may be represented by theformula 0 -0 R26— N’ — CH3 ch3 wherein ν ί '<>2 9 0 45 R26 represents a mixture of alkyls of from about six to thirtycarbons, inclusive, preferably from about twelve to twenty carbons,inclusive; (h) formula IX which is a fatty alcohol polyglycol ether, 5 (the fatty alcohol polyglycol ether may be represented by the formula R27 — O(CHCH2)z2 — OH wherein R27 represents a mixture of alkyls of from about six to thirty carbons,inclusive, preferably from about twelve to twenty carbons, inclusive; R'is of hydrogen or alkyl of from one to two carbons; 15 Z2 represents the number of moles of ethoxylation in the formula and are when taken together about from one to fifty, preferably five to’ifteen) (i) formula X which is a fatty acid esterified polyethoxyether,or which is s:earic acid polyethoxylate, 20 the coco esterfied polyethoxyether and stearic acid polyethoxylate may be represented by the formula r2S_C02 — (EO)z3- H wtierein R2S represents a mixture of alkyls of from about twelve to twenty carbons inclusive; 46 Vί 0 2 9 0 ΕΟ représente ethoxylation in the formula and Z3 is fforn five tofifteen; (j) formula XI which is a quatemary ammoniummay berepresented by the formula 5 R29-N+(CH3)2(CH2(C6H5)) Q‘ wherein R2g représente alkyl from CIO to C16 and Q is anagronomically acceptable anion; (k) formula XII which is a quatemary ammonium represented by10 the formula R30R3iR32N+(EO)ni(PO^2 Q’ wherein Rso, R31 and R32 are ail methyl or one of R30, R31, R32 is((EO)ni(PO)n2); EO is ethylene oxide; PO is propylene oxide; ni is an 15 integer of one to two; and n2 is an integer of about six to ten; and Q is anagronomically acceptable anion); (l) formula XIII which is diamine ethoxylaterepresented by theformula R33 20 \ (EO)n5

25 wherein R33 represents alkyl of from about CIO to C16; and n3,114, nsrepresent the number of moles of ethoxylation in the formula and arewhen xaken together about from five to fifteen; (nf formula XI which is an alkoxylated primary fatty alcohol,represented by the formula R—OiPO^tEO^ 30 47 Wherein represents alkyl of from about C13 to C15; EO is ethylene oxide: PO represents propylene oxide; n6 is an integer of from about 6 to 9: n7 is an integer from about 4.5 to 6; and G) mixtures thereof.

4. A composition of Claim 2 wherein the formula is (a) the alkyl glycosides which is C9 to C11 alkyl 1.6 polyglycosidewhere the number of glycoside groups is one to two and the alkyl group is a mixtureof from nine to eleven carbons; (b) the quaternized fatty amine ethoxylate is cocomethyl ammoniumchloride or coco dimethyl diethoxylated ammonium chloride; (c) a mixture which is blend of fatty amine ethoxylate + nonylphenolethoxylate; (e) the secondary alcohol ethoxylate is 15 carbon branched secondaryalcoho! 9 molar ethoxylate, or 15 carbon secondary alcohol 12 molar ethoxylate; (f) mixtures thereof;

5 A composition of claim 4 wherein the adujuvant is the alkyl glycosides cf the formula II wherein the alkyl group is a mixture of from aoout nine to eleven carbons, inclusive, and the number of glycos de groups présent in the formula are from one to two.

6 A composition of claim 5 wherein the formula I is N-(3,4,4-trifluoro- 3-butenyl) g ycine or the monohydrochloride sait thereof.

7 A composition cf claim 5 wherein the formula I is 3,4,4-trifluoro-3- butene-1 -amine, cr the monohydrochloride sait thereof.

8. A composition for controlling nematode, insect, or acarid infestation of a plant comprising an effective amount of a composition of Claim 1 in an agroncmicaky acceptable carrier.

9 A composition for controlling nematode, insect, or acarid infestation of a plant comprismg an effective amount of a composition of claim 5 in an agronom: cally acceptable carrier.

10. A composition for controlling nematode. insect, or acarid infestaoon cr a plant comprising an effective amount of a composition of claim 6 in an agmnomically acceptable carrier. 48 o ns 2 9 Ο

11. A composition for controlling nematode, insect, or acaridinfestation of a plant comprising an effective amount of a compositionof claim 7 in an agronomically acceptable carrier.

12. A method of controlling nematode, insect, or acarid infestation of a 5 plant, comprising applying to a plant locus an effective amount of a composition of claim 1.

13. A method of systemically controlling nematode, insect or acaridinfestation of a plant, comprising applying to a plant locus an effectiveamount of a composition of claim 9 that has or is transformed after 10 application to hâve polarity providing phloem mobility withoutreducing nematode-controlling effectiveness.

14. A method of claim 12 wherein the compound of the formula I in thecomposition is N-(3,4,4-trifluoro-3-butenyl)glycine or themonohvdrochloride sait thereof.

15 15. A method of claim 12 wherein the compound of the formula I in thecomposition is 3,4,4-trifluoro-3-butene-l-amine, or themonohvdrochloride sait thereof.