IP Library › Granted Patent US 9,249,133

Granted Patent B2

US 9,249,133 · App. 14/208,394 · Granted Feb 2, 2016

Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto

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Patent No.: US 9,249,133
App. No.: 14/208,394
Granted: Feb 2, 2016
Kind: B2

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Abstract

This disclosure relates to the field of molecules having pesticidal utility against pests in phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and/or molluscicides. This document discloses molecules having the following formula (“Formula One”).

Claims (36)

1. A process comprising reacting 2-iminolthiazolidin-4-one (3-1a) with an isocyanate (1-2) to produce thiobiuret (3-1′)

wherein

(A) Ar 1 is selected from

(1) phenyl, pyridazinyl, pyridyl, pyrimidinyl, or

(2) substituted phenyl, substituted pyridazinyl, substituted pyridyl, or substituted pyrimidinyl,

wherein said substituted phenyl, substituted pyridazinyl, substituted pyridyl, and substituted pyrimidinyl, have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(B) Het is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring, containing one or more heteroatoms independently selected from nitrogen, sulfur, or oxygen, and where Ar 1 and Ar 2 are not ortho to each other (but may be meta or para, such as, for a five-membered ring they are 1, 3 and for a 6-membered ring they are either 1, 3 or 1, 4) and where said heterocyclic ring may also be substituted with one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), phenyl, and phenoxy;

(1) phenyl, pyridazinyl, pyridyl, pyrimidinyl, or

(2) substituted phenyl, substituted pyridazinyl, substituted pyridyl, or substituted pyrimidinyl,

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(D) R 1 is selected from H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)OC(═O)(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), and (C 1 -C 6 alkyl)OC(═O)O(C 1 -C 6 alkyl),

wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, and alkynyl are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(E) R 2 is selected from (J), H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(═O)(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C 1 -C 6 alkylphenyl, C 1 -C 6 alkyl-O-phenyl, C(═O)(Het-1), (Het-1), (C 1 -C 6 alkyl)-(Het-1), C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)(C 1 -C 6 alkyl), C 1 -C 6 alkyl-O—C(═O)OC 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)NR x R y , C 1 -C 6 alkyl C(═O)N(R x )C 1 -C 6 alkyl-(Het-1), C 1 -C 6 alkylC(═O)(Het-1), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )(R y ))(C(═O)OH), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )(R y ), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )C(═O)—O—C 1 -C 6 alkyl)(C(═O)OH), C 1 -C 6 alkylC(═O)(Het-1)C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl-O—C(═O)(Het-1), C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-NR x R y , (C 1 -C 6 alkyl)S-(Het-1) or C 1 -C 6 alkyl-O-(Het-1),

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and (Het-1) are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , NR x R y , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, Si(C 1 -C 6 alkyl) 3 , S(═O) n NR x R y , or (Het-1);

(F) R 3 is selected from phenyl, C 1 -C 6 alkylphenyl, C 1 -C 6 alkyl-O-phenyl, C 2 -C 6 alkenyl-O-phenyl, (Het-1), C 1 -C 6 alkyl(Het-1), or C 1 -C 6 alkyl-O-(Het-1),

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and (Het-1) are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , NR x R y , C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), O(C 1 -C 6 alkyl), S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, and (Het-1);

(G) R 4 is selected from (J), H, or C 1 -C 6 alkyl;

(H) Q 1 is selected from O or S,

(I) R x and R y are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), and phenyl,

wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, alkynyl, phenyl, phenoxy, and (Het-1), are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, halophenyl, phenoxy, and (Het-1),

or R x and R y together can optionally form a 5- to 7-membered saturated or unsaturated cyclic group which may contain one or more heteroatoms selected from nitrogen, sulfur, and oxygen, and where said cyclic group may be substituted with F, Cl, Br, I, CN, oxo, thioxo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, substituted phenyl, phenoxy, and (Het-1);

(J) R 2 and R 4 may be a 1- to 4-membered saturated or unsaturated, hydrocarbyl link, which may contain one or more heteroatoms selected from nitrogen, sulfur, and oxygen, and together with C x (Q 1 )(N x ) forms a cyclic structure, wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from R 5 , R 6 , and R 7 , wherein each R 5 , R 6 , and R 7 is selected from H, F, Cl, Br, I, CN, OH, C 1 -C 6 alkyl, oxo, thioxo, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, substituted phenyl, phenoxy, or (Het-1);

(K) (Het-1) is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring, containing one or more heteroatoms independently selected from nitrogen, sulfur or oxygen, wherein said heterocyclic ring may also be substituted with one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy,

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), phenyl, and phenoxy;

(L) L is linker selected from

(1) a saturated or unsaturated, substituted or unsubstituted, linear (C 1 -C 4 )hydrocarbyl linker, or

(2) a saturated or unsaturated, substituted or unsubstituted, cyclic (C 3 -C 8 )hydrocarbyl group linker,

wherein each of said linkers connects Ar 2 to N y and

wherein said substituted linear (C 1 -C 4 )hydrocarbyl linker and substituted cyclic (C 3 -C 8 )hydrocarbyl linker has one or more substituents independently selected from R 8 , R 9 , R 10 , R 11 , and R 12 , wherein each R 8 , R 9 , R 10 , R 11 , and R 12 , is selected from F, Cl, Br, I, CN, oxo, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 halocycloalkyl, or phenyl; and

(M) n is each individually 0, 1, or 2.

2. A process comprising reacting 2-iminothiazolidin-2-one (3-1a) with 4-nitrophenyl chloroformate, to produce 4-nitrophenyl carbamate intermediate (3-2a), followed by reacting 4-nitrophenyl carbamate intermediate (3-2a) with a primary alkyl amine Ar 1 -Het-Ar 2 -L-NHR 1 , wherein R 1 is H or alkyl, to produce thiobiuret (3-1′)

wherein R 3 , R 5 , Ar 1 , Het, Ar 2 , and L are previously disclosed in claim 1 .

Assignments (2)

CHANGE OF NAME Recorded Nov 8, 2021

From: DOW AGROSCIENCES LLC

To: CORTEVA AGRISCIENCE LLC

Reel/Frame 058044/0184 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2014

From: FISCHER, LINDSEY G; WARD, ANDREW L; ROSS, RONALD, JR; GIAMPIETRO, NATALIE C; DEAMICIS, CARL; HAO, YAN; CROUSE, GARY D; SPARKS, THOMAS C; BAUM, ERICH W; PETKUS, JEFF

To: DOW AGROSCIENCES LLC

Reel/Frame 032434/0802 →