Microcapsules comprising cinmethyln in the core and a polyurea derived from diphenylmethane diisocyanate or an oligomer thereof

Patent metadata

Field	Value
Publication number	US-12376586-B2
Application number	US-201816476633-A
Country	US
Kind code	B2
Filing date	Jan 10, 2018
Priority date	Jan 10, 2017
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The present invention relates to microcapsules comprising a core, wherein the core comprises cinmethylin, and a polyurea shell, wherein the shell comprises a polyaddition product of diphenylmethane diisocyanate or an oligomer thereof and at least one amine having at least two primary amino groups; to a composition comprising such microcapsules; to a method for preparing such microcapsules or such a composition; to a composition obtainable by said preparation method; and to the use of such microcapsules or compositions for controlling undesired vegetation.

First claim

We claim:

1. Microcapsules comprising a core, wherein the core comprises cinmethylin, and a shell, wherein the shell comprises a polyurea material which comprises a polyaddition product of (1) polymeric methylene diphenyl diisocyanate having an average functionality in the range of 2.0 to 4.0 and (2) an aliphatic diamine of the formula H 2 N—(CH 2 ) p —NH 2 , wherein p is 6;
where a weight ratio of cinmethylin and the polyurea material of the shell is from 40:1 to 70:1; and
where an overall weight ratio of cinmethylin and the polymeric methylene diphenyl diisocyanate present in the shell in polymerized form is from 50:1 to 120:1.

2. The microcapsules according to claim 1 , where an average particle size d 50 of the microcapsules, as determined according to ISO 13320, Particle Size Analysis-Laser Diffraction Methods, December, 1, 2009, is from 0.5 to 100 μm.

3. A composition comprising microcapsules as defined in claim 1 and a dispersing medium.

4. The composition according to claim 3 , where the dispersing medium is an aqueous medium and the composition is an aqueous dispersion.

5. The composition according to claim 3 , containing the microcapsules in an amount of from 10 to 70% by weight, based on the total weight of the composition.

6. The composition according to claim 3 , further comprising at least one ingredient selected from the group consisting of a surfactant, a dispersing agent, an emulsifier, a wetting agent, an adjuvant, an inorganic salt, a solubilizer, a penetration enhancer, a protective colloid, an adhesion agent, a thickener, a humectant, an antifoam, an antifreeze agent, a stabilizer, an antimicrobial agent, a pigment, a colorant, a buffer, a tackifier, a binder, and combinations thereof.

7. A composition comprising
(i) microcapsules as defined in claim 1 ;
(ii) at least one herbicide different from cinmethylin; and
(iii) optionally a dispersing medium.

8. The composition according to claim 7 , where the at least one herbicide different from cinmethylin is selected from the group consisting of:
(ii.1) herbicides from the group of lipid biosynthesis inhibitors, which are in turn selected from the group consisting of:
ACC-herbicides selected from the group consisting of alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); and 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and
non ACC herbicides selected from the group consisting of benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
(ii.2) herbicides from the group of ALS inhibitors, which are in turn selected from the group consisting of:
sulfonylureas selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron,
imidazolinones selected from the group consisting of imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr,
triazolopyrimidine herbicides and sulfonanilides selected from the group consisting of cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinylbenzoates selected from the group consisting of bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides selected from the group consisting of flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
(ii.3) herbicides from the group of the photosynthesis inhibitors, which are in turn selected from the group consisting of:
amicarbazone,
inhibitors of the photosystem II selected from the group consisting of triazine herbicides, in turn selected from the group consisting of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones in turn selected from the group consisting of ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea herbicides selected from the group consisting of chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron,
phenyl carbamates selected from the group consisting of desmedipham, karbutilat, phenmedipham and phenmedipham-ethyl,
nitrile herbicides selected from the group consisting of bromofenoxim, bromoxynil and its salts

Assignees

• Basf Agro Bv

Inventors

• Urch Henning
• Franz Diana
• Nolte Marc
• Kraemer Gerd
• Michel Amandine
• Kolb Klaus

Classifications

• C07D493/08

  Bridged systems · CPC title

• C08L75/02

  Polyureas · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08G61/10

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title