BIOCIDE COMPOSITIONS, METHODS OF MANUFACTURE, AND METHODS OF USE

1 . A biocide composition comprising:

a biocide, and

an adjuvant comprising a ketal having the formula (1)

wherein

a is 0 or an integer of 1 to 12, specifically 1 to 6, more specifically 1 to 4, still more specifically 2 to 4;

b is 0, 1, or 2;

R is —C(═O)OR 1 or —CH 2 OH;

R 1 is a C 1-18 alkyl or C 5-8 cycloaliphatic or heterocyclic group;

R 2 is a divalent C 1-8 alkylene group optionally substituted with up to 5 hydroxyl groups;

R 3 and R 4 are each independently hydrogen or C 1-6 alkyl; and

R 5 is hydrogen or C 1-3 alkyl.

2 . (canceled)

3 . (canceled)

4 . The biocide composition of claim 1 , wherein R 2 is >CH—CH 3 , >CH—CH 2 OH, >C(CH 3 )CH 2 OH, >C(C 2 H 5 )CH 2 OH, >C(CH 2 OH) 2 , >CH—CH(OH)—CH 2 OH, or >CH—(CHOH) 3 —CH 2 OH.

5 . (canceled)

6 . (canceled)

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8 . The biocide composition of claim 1 , wherein the ketal has the formula (1a)

wherein R 1 is methyl, ethyl, n-propyl, n-butyl, 2-ethylhexyl, 1-nonyl, 3,5,5-trimethylhexyl, or tetrahydrofurfuryl,

or formula (1b)

wherein R 1 is methyl, ethyl, n-propyl, n-butyl, 2-ethylhexyl, 1-nonyl, 3,5,5-trimethylhexyl, or tetrahydrofurfuryl,

or formula (1c)

or formula (1d)

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12 . The biocide composition of claim 1 , wherein the biocide comprises a herbicide, an insecticide, a fungicide, an algicide, a moluscicide, a miticide, a rodenticide, an antimicrobial, a plant growth regulator, or a combination thereof.

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19 . The biocide composition of claim 1 , further comprising an oil, a solvent, a surfactant, a penetrant, water, a wetting agent, an anti-freeze, a preservative, stabilizing agent, a buffer, a rheology modifier, an anti-foam agent, a crystallization inhibitor, a fertilizer, or a combination comprising at least one of the foregoing.

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30 . The biocide composition of claim 1 , wherein the composition is an emulsifiable concentrate, a suspension concentrate, a suspo-emulsion concentrate, a tank mix composition, or a ready-to-use liquid composition.

31 . An emulsifiable concentrate comprising:

the biocide composition of claim 1 ;

a surfactant; and

optionally an oil,

wherein the emulsifiable concentrate comprises, based on the total weight of the composition:

0.01 to 99 weight %, specifically 0.05 to 75 weight %, more specifically 0.1 to 40 weight % of the biocide;

0.1 to 99 weight %, specifically 3 to 80 weight %, more specifically 10 to 70 weight % of the adjuvant;

0.1 to 15 weight %, specifically 1 to 10 weight %, more specifically 1 to 5 weight % of the surfactant; and

0 to 50 weight %, specifically 5 to 30 weight %, more specifically 10 to 25 weight % of the oil.

32 . (canceled)

33 . A suspension concentrate comprising:

the biocide composition of claim 1 ;

water;

a surfactant; and

optionally an oil,

wherein the suspension concentrate comprises, based on the total weight of the composition:

0.1 to 90 weight %, specifically 1 to 60 weight %, more specifically 10 to 50 weight % of the biocide;

5 to 60 weight %, specifically 10 to 50 weight %, more specifically 20 to 40 weight % of the adjuvant;

20 to 60 weight %, specifically 20 to 60 weight %, more specifically 20 to 50 weight % of water;

1 to 35 weight %, specifically 2 to 20 weight %, more specifically 3 to 12 weight % of the surfactant; and

0 to 70 weight %, specifically 10 to 60 weight %, more specifically 20 to 50 weight % of the oil.

34 . (canceled)

35 . A tank mix composition for foliar or soil application, comprising:

the biocide composition of claim 1 ;

water;

a surfactant; and

optionally an oil,

wherein the tank mix composition comprises, based on the total weight of the composition:

0.0005 to 20 weight %, specifically 0.002 to 10 weight %, more specifically 0.005 to 2 weight % of the biocide;

0.0005 to 80 weight %, specifically 0.002 to 40 weight %, more specifically 0.005 to 8 weight % of the adjuvant;

40 to 99 weight %, specifically 50 to 90 weight %, more specifically 50 to 80 weight % water;

0.1 to 30 weight %, specifically 1 to 25 weight %, more specifically 5 to 20 weight % of the surfactant; and

0 to 20 weight %, specifically 1 to 15 weight %, more specifically 1 to 10 weight % of the oil.

36 . (canceled)

37 . A ready-to-use liquid composition comprising:

the biocide composition of claim 1 ;

a solvent other than the adjuvant; and

optionally a thickening agent, a propellant, an attractant, or a combination thereof;

wherein the solvent is 90% vaporized within 5 minutes of application of the composition to a surface,

wherein the ready-to-use liquid comprises, based on the total weight of the composition:

0.0005 to 2 weight %, specifically 0.002 to 1 weight %, more specifically 0.005 to 0.5 weight % of the biocide;

10 to 60 weight %, specifically 20 to 50 weight %, more specifically 30 to 40 weight % of the adjuvant;

10 to 60 weight %, specifically 20 to 50 weight %, more specifically 30 to 40 weight % of the solvent;

0 to 5 weight %, specifically 0.1 to 1 weight %, more specifically 0.5 to 1 weight % of the thickening agent;

0 to 75 weight %, specifically 5 to 50 weight %, more specifically 10 to 30 weight % of the propellant; and

0 to 70 weight %, specifically 5 to 60 weight %, more specifically 10 to 40 weight % of the attractant.

38 . (canceled)

39 . A composition, comprising an adjuvant comprising a ketal having the formula (1)

wherein

a is 0 or an integer of 1 to 12, specifically 1 to 6, more specifically 1 to 4, still more specifically 2 to 4;

b is 0, 1, or 2;

R is —C(═O)OR 1 or —CH 2 OH;

R 1 is a C 1-18 alkyl or C 5-8 cycloaliphatic or heterocyclic group;

R 2 is a divalent C 1-8 alkylene group optionally substituted with up to 5 hydroxyl groups;

R 3 and R 4 are each independently hydrogen or C 1-6 alkyl; and

R 5 is hydrogen or C 1-3 alkyl;

a compound having the formula (6)

wherein S 1 is >C═O (carbonyl) or >CH 2 (methylene), and S 2 is C 1-12 alkyl, C 6-20 cycloalkyl, or C 6-20 aryl;

a compound having the formula (7) or (8)

a compound having the formula (11)

wherein

a is 0 or an integer of 1 to 12;

R is —CH 2 OH; and

R 5 is hydrogen or C 1-3 alkyl;

a compound having the formula (3)

wherein

a is 0 or an integer of 1 to 12;

R 1 is a C 1-18 alkyl or C 5-8 cycloaliphatic or heterocyclic group; and

R 5 is hydrogen or C 1-3 alkyl;

or a combination thereof,

wherein the composition is a crop oil concentrate or a seed treatment composition.

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42 . The composition of claim 39 comprising, based on the total weight of the composition:

1 to 99 weight %, specifically 10 to 90 weight %, more specifically 20 to 80 weight % of the adjuvant;

1 to 40 weight %, specifically 2 to 20 weight %, more specifically 2 to 10 weight % of a surfactant; and

0 to 95 weight %, specifically 5 to 90 weight %, more specifically 10 to 80 weight % of an oil,

wherein the composition is a crop oil concentrate.

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46 . The seed treatment composition of claim 39 , further comprising a biocide, a polymeric binder, water or a combination thereof and comprising, based on the total weight of the seed treatment composition:

1 to 70 weight %, specifically 1 to 60 weight %, more specifically 5 to 50 weight % of the biocide;

1 to 90 weight %, specifically 10 to 60 weight %, more specifically 15 to 50 weight % of the adjuvant;

5 to 70 weight %, specifically 15 to 65 weight %, more specifically 15 to 60 weight % of the polymeric binder; and

1 to 90 weight %, specifically 10 to 60 weight %, more specifically 15 to 50 weight % water.

47 . A method of controlling a pest, the method comprising contacting the pest or the locus of the pest with the biocide composition of claim 1 , in an amount effective to control the pest.

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51 . A biocide composition comprising:

a biocide, and

an adjuvant comprising a compound having the formula (11)

wherein

a is 0 or an integer of 1 to 12;

R is —CH 2 OH; and

R 5 is hydrogen or C 1-3 alkyl,

a compound having the formula (3)

wherein

a is 0or an integer of 1 to 12;

R 1 is a C 1-18 alkyl or C 5-8 cycloaliphatic or heterocyclic group; and

R 5 is hydrogen or C 1-3 alkyl,

a compound having the formula (6)

wherein S 1 is >C═O (carbonyl) or >CH 2 (methylene), and S 2 is C 1-12 alkyl, C 6-20 cycloalkyl, or C 6-20 aryl;

a compound having the formula (7)

a compound having the formula (8)

or a combination thereof.

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53 . The biocide composition of claim 51 , wherein R 5 in formula (11) is methyl; and a in formula (11) is 2 or 3.

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57 . The biocide composition of claim 51 , wherein R 5 in formula (3) is methyl; and a in formula (3) is 1, 2, 3, or 4.

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67 . The biocide composition of claim 51 , wherein the adjuvant comprises the compound having the formula (6) wherein S 2 is methyl, ethyl, butyl, octyl, decyl, dodecyl, phenyl, 4-methylphenyl, or cyclohexyl.

68 . The biocide composition of claim 51 , wherein the adjuvant comprises the compound having the formula (6) wherein S 1 is >C═O (carbonyl) or >CH 2 (methylene) and S 2 is methyl, ethyl, butyl, octyl, decyl, dodecyl, phenyl, 4-methylphenyl, or cyclohexyl.

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70 . The biocide composition of claim 51 , wherein the adjuvant comprises the compound of formula (9)

or compound of formula (10)

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